Sodium hydride → [Rac]-2-{4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-propionic acid tert-butyl ester

HRID 1767878Notes

Reaction equation

HRID 1767878 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2.[C:28]([O:32][C:33](=[O:37])[CH:34](Br)[CH3:35])([CH3:31])([CH3:30])[CH3:29].[H-].[Na+]>>[C:28]([O:32][C:33](=[O:37])[CH:34]([N:13]1[C:14]2[C:10](=[C:9]([O:8][CH2:7][C:6]3[S:5][C:4]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=4)=[N:3][C:2]=3[CH3:1])[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1)[CH3:35])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 545327tert-Butyl 2-bromopropanoateHCID 115746051H-Indole, 4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]methoxy]-

Product 1

HCID 69283091[Rac]-2-{4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-propionic acid tert-butyl ester

Procedure

In analogy to the procedure described in example 1 b], 4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole (example 1 a]) was reacted with 2-bromo-propionic acid tert-butyl ester in the presence of sodium hydride to obtain [rac]-2-{4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-propionic acid tert-butyl ester as yellow oil.

Sources & evidence

ORD record
ord-defed28e5ab44cb59416be79d80b3ebf
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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