Sodium hydride → 3-{2-Methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-phenyl}-propionic acid methyl ester

HRID 854571Notes

Reaction equation

HRID 854571 reaction equation
I[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:18].[CH3:19][O:20][C:21](=[O:33])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][C:25]=1[CH3:32].[H-].[Na+]>CN(C=O)C>[CH3:19][O:20][C:21](=[O:33])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][CH2:2][C:3]2[S:7][C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)=[N:5][C:4]=2[CH3:18])=[CH:26][C:25]=1[CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 236145065-(Iodomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazoleHCID 574319763-(4-Hydroxymethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

Product 1

HCID 694701053-{2-Methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-phenyl}-propionic acid methyl esterYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Iodomethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (0.14 g, 0.37 mmol) and 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic acid methyl ester (0.064 g, 0.31 mmol) in DMF (1 mL) is added sodium hydride (60% dispersion, 0.036 g, 1.50 mmol). The mixture is stirred at RT for 3 h. The reaction is quenched with water, and the mixture is extracted with EtOAc. The organics are dried with MgSO4 and concentrated. The crude material is purified by flash chromatography to yield the title compound (0.022 g, 16%).

Workup

  1. customThe reaction is quenched with water
  2. extractionthe mixture is extracted with EtOAc
  3. dry with materialThe organics are dried with MgSO4
  4. concentrationconcentrated
  5. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-2f3d8ca05caf44548dce3de24141049a
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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