Sodium hydride → (6-{2-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-indol-1-yl)-acetic acid tert-butyl ester

HRID 1767943Notes

Reaction equation

HRID 1767943 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[S:5][C:6]=1[CH2:7][CH2:8][O:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:19][CH2:20][CH3:21])=[CH:15][NH:16]2)=[CH:12][CH:11]=1.Br[CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[H-].[Na+]>>[C:37]([O:36][C:34](=[O:35])[CH2:33][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([O:9][CH2:8][CH2:7][C:6]3[S:5][C:4]([C:22]4[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=4)=[N:3][C:2]=3[CH3:1])[CH:18]=2)[C:14]([CH2:19][CH2:20][CH3:21])=[CH:15]1)([CH3:40])([CH3:39])[CH3:38]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 236145086-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-1H-indole

Product 1

HCID 23614509(6-{2-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-indol-1-yl)-acetic acid tert-butyl ester

Procedure

In analogy to the procedure described in example 3 a], 6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-1H-indole was reacted with tert-butyl bromoacetate in the presence of sodium hydride to obtain (6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-3-propyl-indol-1-yl)-acetic acid tert-butyl ester as colorless oil.

Sources & evidence

ORD record
ord-fdcb0cf7e914418586ab8c955beeb090
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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