appendix 1. nmr data
TRANSCRIPT
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Appendix 1. NMR data
Figure 6.1.1. 1H NMR of methyl 3-amino-4-bromobenzoate (48).
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Figure 6.1.2. 1H NMR of 2-bromo-4,5-dimethoxyaniline (50).
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Figure 6.1.3. 1H NMR of 1,2-dimethoxy-4-nitro-5-(phenylethynyl)benzene (51).
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Figure 6.1.4. 1H NMR of 4,5-dimethoxy-2-(phenylethynyl)aniline (52).
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Figure 6.1.5. 13
C NMR of 4,5-dimethoxy-2-(phenylethynyl)aniline (52).
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Figure 6.1.6. 1H NMR of methyl 4-[(4-methoxyphenyl)ethynyl]-3-nitrobenzoate (53).
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Figure 6.1.7. 13
C NMR of methyl 4-[(4-methoxyphenyl)ethynyl]-3-nitrobenzoate (53).
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Figure 6.1.8. 1H NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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Figure 6.1.9. 13
C NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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Figure 6.1.10. 13
C DEPT-135 NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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Figure 6.1.11. 1H-
13C HSQC NMR of methyl 3-amino-4-[(4-methoxyphenyl)ethynyl]benzoate (54).
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Figure 6.1.12. 1H NMR of tert-butyl [4,5-dimethoxy-2-(phenylethynyl)phenyl]carbamate (55).
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Figure 6.1.13. 13
C NMR of tert-butyl [4,5-dimethoxy-2-(phenylethynyl)phenyl]carbamate (55).
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Figure 6.1.14. 13
C DEPT-135 NMR of tert-butyl [4,5-dimethoxy-2-(phenylethynyl)phenyl]carbamate (55).
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Figure 6.1.15. 1H NMR of N-[4,5-dimethoxy-2-(phenylethynyl)phenyl]-4-methylbenzenesulfonamide (56).
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Figure 6.1.16. 13
C NMR of N-[4,5-dimethoxy-2-(phenylethynyl)phenyl]-4-methylbenzenesulfonamide (56).
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Figure 6.1.17. 13
C DEPT-135 NMR of N-[4,5-dimethoxy-2-(phenylethynyl)phenyl]-4-methylbenzenesulfonamide
(56).
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Figure 6.1.18. 1H NMR of 2-(phenylethynyl)aniline (58).
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Figure 6.1.19. 13
C NMR of 2-(phenylethynyl)aniline (58).
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Figure 6.1.20. 1H NMR of methyl 2-(4-methoxyphenyl)indole-6-carboxylate (59).
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Figure 6.1.21. 1H NMR of 5,6-dimethoxy-2-phenylindole (60).
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Figure 6.1.22. 13
C NMR of 5,6-dimethoxy-2-phenylindole (60).
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Figure 6.1.23. 1H NMR of tert-butyl 2-phenylindole-1-carboxylate (62).
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Figure 6.1.24. 13
C NMR of tert-butyl 2-phenylindole-1-carboxylate (62).
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Figure 6.1.25. 1H NMR of 1-[(4-methylphenyl)sulfonyl]-2-phenylindole (63).
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Figure 6.1.26. 13
C NMR of 1-[(4-methylphenyl)sulfonyl]-2-phenylindole (63).
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Figure 6.1.27. 13
C DEPT-135 NMR of 1-[(4-methylphenyl)sulfonyl]-2-phenylindole (63).
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Figure 6.1.28. 1H NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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Figure 6.1.29. 13
C NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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Figure 6.1.30. 13
C DEPT-135 NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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Figure 6.1.31. 1H-
1H COSY NMR of 1-tert-butyl 2-ethyl 6-methoxyindole-1,2-dicarboxylate (65).
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Figure 6.1.32. 1H NMR of tert-butyl 3-bromo-2-phenylindole-1-carboxylate (66).
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Figure 6.1.33. 13
C NMR of tert-butyl 3-bromo-2-phenylindole-1-carboxylate (66).
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Figure 6.1.34. 13
C DEPT-135 NMR of tert-butyl 3-bromo-2-phenylindole-1-carboxylate (66).
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Figure 6.1.35. 1H NMR of 3-bromo-1-[(4-methylphenyl)sulfonyl]-2-phenylindole (67).
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Figure 6.1.36. 13
C NMR of 3-bromo-1-[(4-methylphenyl)sulfonyl]-2-phenylindole (67).
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Figure 6.1.37. 13
C DEPT-135 NMR of 3-bromo-1-[(4-methylphenyl)sulfonyl]-2-phenylindole (67).
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Figure 6.1.38. 1H NMR of 3-bromo-1-methyl-2-phenylindole (69).
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Figure 6.1.39. 13
C NMR of 3-bromo-1-methyl-2-phenylindole (69).
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Figure 6.1.40. 13
C DEPT-135 NMR of 3-bromo-1-methyl-2-phenylindole (69).
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Figure 6.1.41. 1H NMR of ethyl 3-bromoindole-2-carboxylate (71).
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Figure 6.1.42. 13
C NMR of ethyl 3-bromoindole-2-carboxylate (71).
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Figure 6.1.43. 13
C DEPT-135 NMR of ethyl 3-bromoindole-2-carboxylate (71).
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Figure 6.1.44. 1H-
1H COSY NMR of ethyl 3-bromoindole-2-carboxylate (71).
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Figure 6.1.45. 1H NMR of 1-tert-butyl 2-ethyl 3-bromoindole-1,2-dicarboxylate (72).
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Figure 6.1.46. 13
C NMR of 1-tert-butyl 2-ethyl 3-bromoindole-1,2-dicarboxylate (72).
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Figure 6.1.47. 13
C DEPT-135 NMR of 1-tert-butyl 2-ethyl 3-bromoindole-1,2-dicarboxylate (72).
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Figure 6.1.48. 1H NMR of tris(3,5-dimethoxyphenyl)amine (76).
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Figure 6.1.49. 13
C NMR of tris(3,5-dimethoxyphenyl)amine (76).
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Figure 6.1.50. 13
C DEPT-135 NMR of tris(3,5-dimethoxyphenyl)amine (76).
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Figure 6.1.51. 1H NMR of 2,4,6-trimethylbenzoyl chloride (74).
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Figure 6.1.52. 1H NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium tetrafluoroborate
(77).
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Figure 6.1.53. 13
C NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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Figure 6.1.54. 19
F NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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Figure 6.1.55. 13
C DEPT-135 NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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Figure 6.1.56. 1H-
1H COSY NMR of 10-(3,5-dimethoxyphenyl)-9-mesityl-1,3,6,8-tetramethoxyacridinium
tetrafluoroborate (77).
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Figure 6.1.57. 1H NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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Figure 6.1.58. 13
C NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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Figure 6.1.59. 13
C DEPT-135 NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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Figure 6.1.60. 1H-
1H COSY NMR of 1,1'-methylenebis(2-bromo-4-tert-butylbenzene) (79).
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Figure 6.1.61. 1H NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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Figure 6.1.62. 13
C NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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Figure 6.1.63. 13
C DEPT-135 NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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Figure 6.1.64. 1H-
1H COSY NMR of bis(2-bromo-4-tert-butylphenyl)methanol (80).
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Figure 6.1.65. 1H NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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Figure 6.1.66. 13
C NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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Figure 6.1.67. 13
C DEPT-135 NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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Figure 6.1.68. 1H-
1H COSY NMR of bis(2-bromo-4-tert-butylphenyl)methanone (81).
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Figure 6.1.69. 1H NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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Figure 6.1.70. 13
C NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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Figure 6.1.71. 13
C DEPT-135 NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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Figure 6.1.72. 1H-
1H COSY NMR of 3,6-di-tert-butyl-10-phenylacridin-9(10H)-one (82).
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Figure 6.1.73. 1H NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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Figure 6.1.74. 13
C NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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Figure 6.1.75. 19
F NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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Figure 6.1.76. 13
C DEPT-135 NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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Figure 6.1.77. 1H-
1H COSY NMR of 3,6-di-tert-butyl-9-mesityl-10-phenylacridinium tetrafluoroborate (83).
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Figure 6.1.78. 1H NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.79. 13
C NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.80. 13
C DEPT-135 NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.81. 13
C DEPT-90 NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.82. 1H-
1H COSY NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.83. 1H-
1H NOESY NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.84. 1H-
13C HSQC NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.85. 1H-
13C HMBC NMR of tert-butyl 3-(1-methylpyrrol-2-yl)-2-phenylindole-1-carboxylate (84).
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Figure 6.1.86. 1H NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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Figure 6.1.87. 13
C NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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Figure 6.1.88. 13
C DEPT-135 NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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Figure 6.1.89. 1H-
1H COSY NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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Figure 6.1.90. 1H-
1H NOESY NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
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Figure 6.1.91. 1H-
13C HSQC NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
![Page 92: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/92.jpg)
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Figure 6.1.92. 1H-
13C HMBC NMR of ethyl 3-(1-methylpyrrol-2-yl)indole-2-carboxylate (85).
![Page 93: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/93.jpg)
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Figure 6.1.93. 1H NMR of 1-methyl-3-(1-methylpyrrol-2-yl)-2-phenylindole (86).
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Figure 6.1.94. 1H NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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Figure 6.1.95. 13
C NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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Figure 6.1.96. 13
C DEPT-135 NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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Figure 6.1.97. 1H-
1H COSY NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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Figure 6.1.98. 1H-
1H NOESY NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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Figure 6.1.99. 1H-
13C HSQC NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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Figure 6.1.100. 1H-
13C HMBC NMR of 1-tert-butyl 2-ethyl 3-(1-methylpyrrol-2-yl)indole-1,2-dicarboxylate (87).
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Figure 6.1.101. 1H NMR of tert-butyl 3-(5-methylfuran-2-yl)-2-phenylindole-1-carboxylate (89).
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Figure 6.1.102. 1H-
1H COSY NMR of tert-butyl 3-(5-methylfuran-2-yl)-2-phenylindole-1-carboxylate (89).
![Page 103: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/103.jpg)
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Figure 6.1.103. 1H-
1H NOESY NMR of tert-butyl 3-(5-methylfuran-2-yl)-2-phenylindole-1-carboxylate (89).
![Page 104: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/104.jpg)
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Figure 6.1.104. 1H NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-carboxylate (91).
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Figure 6.1.105. 13
C NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-carboxylate (91).
![Page 106: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/106.jpg)
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Figure 6.1.106. 13
C DEPT-135 NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
![Page 107: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/107.jpg)
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Figure 6.1.107. 13
C DEPT-90 NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
![Page 108: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/108.jpg)
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Figure 6.1.108. 1H-
1H COSY NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-carboxylate
(91).
![Page 109: Appendix 1. NMR data](https://reader030.vdocuments.mx/reader030/viewer/2022012117/61dd2ef8fba0fd2f0b497d53/html5/thumbnails/109.jpg)
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Figure 6.1.109. 1H-
1H NOESY NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
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Figure 6.1.110. 1H-
13C HMBC NMR of tert-butyl 3-(4,5-dimethoxy-2-methylphenyl)-2-phenylindole-1-
carboxylate (91).
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Figure 6.1.111. 1H NMR of 3-bromo-2-phenylindole (88).