methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate → methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

HRID 1807631Notes

Reaction equation

HRID 1807631 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]([CH3:34])[C:17]2[C:22]([C:23]=1[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[CH:21][CH:20]=[C:19]([C:30]([O:32][CH3:33])=[O:31])[CH:18]=2)C1C=CC=CC=1>CO.CC(O)=O.[OH-].[Pd+2].[OH-]>[CH:24]1([C:23]2[C:22]3[C:17](=[CH:18][C:19]([C:30]([O:32][CH3:33])=[O:31])=[CH:20][CH:21]=3)[N:16]([CH3:34])[C:15]=2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 1

HCID 58317811methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate

Product 1

HCID 58317807methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of intermediate 3 (4.00 g) in MeOH (36 mL) and AcOH (4 mL) was hydrogenated in presence of palladium hydroxide as catalyst. After 12 h, the reaction mixture was filtered and the filtrate was evaporated to give methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate 4: m/z=364 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-97af318f38d644538868cff344fee77a
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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