Sodium Hydroxide → 3-(Cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylic acid

HRID 1006284Notes

Reaction equation

HRID 1006284 reaction equation
[C:1]1(=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[C:6]=2[C:25]([O:27]CC)=[O:26])[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1>[C:1]1(=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=3)[C:6]=2[C:25]([OH:27])=[O:26])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22676741Ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate

Product 1

HCID 101337923-(Cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylic acidYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound was prepared from ethyl 3-(cyclopropylidenemethyl)-1-[3-(trifluoromethyl)benzyl]-1H-indole-2-carboxylate (Example 182) using the method described in Example 229, except 6N aqueous sodium hydroxide solution was used with tetrahydrofuran as a co-solvent. Flash chromatography of the residue over silica gel using 50% ethyl acetate/hexane gave the title compound (57%) as a pale yellow solid (mp=148-150° C). The product had: 1H NMR (300 MHz, acetone-d6) δ 11.70 (s, 1 H), 8.16 (d, 1 H), 7.70 (s, 1 H), 7.56-7.46 (m, 4 H), 7.35-7.27 (m, 2 H), 7.19-7.15 (m, 1 H), 5.98 (s, 2 H), 1.58-1.53 (m, 2 H), 1.33-1.28 (m, 2 H); mass spectroscopy gave MH+=372.1 (calcd exact mass for C21H16F3NH2=371.11).

Sources & evidence

ORD record
ord-560a01e5bfec40ecb3648b8b4a920668
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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