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

HRID 1767987Notes

Reaction equation

HRID 1767987 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]3[S:17][C:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=4)=[N:15][C:14]=3[CH3:28])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].[H-].[Na+]>>[C:34]([O:33][C:31](=[O:32])[CH2:30][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]3[S:17][C:16]([C:18]4[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:22][CH:23]=4)=[N:15][C:14]=3[CH3:28])[CH:6]=2)[C:2]([CH3:1])=[CH:3]1)([CH3:37])([CH3:36])[CH3:35]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 236144963-methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole

Product 1

HCID 69280387{3-Methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

Procedure

In analogy to the procedure described in example 27 f], 3-methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole was reacted with tert-butyl bromoacetate in the presence of sodium hydride to obtain {3-methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester as brown oil.

Sources & evidence

ORD record
ord-3f920a36d571426fadc20afd81f86375
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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