10-tert-butyl 6-methyl 13-cyclohexyl-3-fluoro-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate → 10-tert-butyl 6-methyl 13-cyclohexyl-3-fluoro-5-methyl-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate

HRID 1486422Notes

Reaction equation

HRID 1486422 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][C:17]4[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:37](C1C=C(F)C=CC=1C1NC2C(C=1C1CCCCC1)=CC=C(C(OC(C)(C)C)=O)C=2)(=O)C>>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([CH3:37])[C:17]4[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 5824477710-tert-butyl 6-methyl 13-cyclohexyl-3-fluoro-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylateHCID 58244778HCID 58244778, compound

Product 1

HCID 5824477310-tert-butyl 6-methyl 13-cyclohexyl-3-fluoro-5-methyl-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylateYield 11%

Procedure

The title product 10-tert-butyl 6-methyl 13-cyclohexyl-3-fluoro-5-methyl-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate 20a was synthesized following the procedure reported for the synthesis of 10-tert-butyl 6-methyl 13-cyclohexyl-3-fluoro-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate 19a, using tert-butyl 2-(2-acetyl-4-fluorophenyl)-3-cyclohexyl-1H-indole-6-carboxylate 33c instead of tert-butyl 3-cyclohexyl-2-(4-fluoro-2-formylphenyl)-1H-indole-6-carboxylate 32d, and was obtained in 11% yield as a white solid; m/z 504 [M+H]+.

Workup

  1. customwas obtained in 11% yield as a white solid

Sources & evidence

ORD record
ord-8e12988075e04353bb4f7f7aacf6c9ad
Source dataset
uspto-grants-2016_08
Patent number
US09427440B2

Reaction notes

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