Dichloromethane → 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylic acid

HRID 1807641Notes

Reaction equation

HRID 1807641 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:23])[C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCl>>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:23])[C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 58317834tert-butyl 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylate

Product 1

HCID 583177963-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylic acidYield 96%

Procedure

To a solution of tert-butyl 3-cyclohexyl-2-(2-(2-methoxy-2-oxoethoxy)phenyl)-1-methyl-1H-indole-6-carboxylate 26 (0.7 g, 1.46 mmol), in dichloromethane 50 mL tri-fluoro-acetic acid (4.2 g, 36.6 mmol) was added. The resulting mixture was stirred at room temperature for 12 hours. The solvent was removed then the residue was purified by column chromatography using dichloromethane/methanol to yield 0.59 g (96%) of 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylic acid 27: m/z=422 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0f6276747a5441ba891035b17548154c
Source dataset
uspto-grants-2013_01
Patent number
US08357687B2

Reaction notes

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