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

HRID 1767938Notes

Reaction equation

HRID 1767938 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][CH2:13][C:14]3[S:18][C:17]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=4)=[N:16][C:15]=3[CH3:29])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[H-].[Na+]>>[C:35]([O:34][C:32](=[O:33])[CH2:31][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C:14]3[S:18][C:17]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=4)=[N:16][C:15]=3[CH3:29])[CH:6]=2)[C:2]([CH3:1])=[CH:3]1)([CH3:38])([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 236144953-methyl-6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-1H-indole

Product 1

HCID 69279704(3-Methyl-6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-indol-1-yl)-acetic acid tert-butyl ester

Procedure

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

Sources & evidence

ORD record
ord-70f64869561f4c2581d76cc996891773
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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