Potassium Carbonate → HCID 68492752, compound

HRID 1879216Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[NH:12][N:13]=[CH:14][CH:15]=2)=[N:8][C:7]=1[CH3:16])=[O:5])[CH3:2].Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:12]=2)=[N:8][C:7]=1[CH3:16])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid ethyl ester (2.5 g, 10.54 mmol) in dimethyl sulfoxide (50 mL) was treated with 1-(2-bromo-ethyl)-4-fluoro-benzene (2.10 g, 10.54 mmol) and potassium carbonate (4.30 g, 31.64 mmol), and the reaction mixture was heated to 90° C. for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), and washed with brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography (hexanes:ethyl acetate, 1:1) to provide 2-{1-[2-(4-fluoro-phenyl)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid ethyl ester as a white solid (1.57 g, 45% yield). MS (M+H)+=360; Rt=1.65 min.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with brine (2×100 mL)
dry with materialThe organic phase was dried (Na2SO4)
customevaporated
customThe residue was purified by flash column chromatography (hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record: ord-20cf1609ed794a77a84065d63636e909
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314138B2

Reaction notes

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