Potassium Carbonate → HCID 59489552, compound

HRID 1879222Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[NH:17][N:18]=[CH:19][CH:20]=2)=[N:13][C:12]=1[CH3:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:32]=[CH:31][C:26]([O:27][CH2:28][CH2:29]Br)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:20]=[CH:19][N:18]([CH2:29][CH2:28][O:27][C:26]3[CH:31]=[CH:32][C:23]([F:22])=[CH:24][CH:25]=3)[N:17]=2)=[N:13][C:12]=1[CH3:21])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid benzylamide (0.2 g, 0.61 mmol) in dimethyl sulfoxide (5 mL) was treated with 4-fluorophenoxyethyl bromide (0.14 g, 0.67 mmol) and potassium carbonate (0.30 g, 2.0 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 (50 mL), and washed with brine (2×50 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (methylene chloride:methanol, 95:5) to provide 2-{1-[2-(4-fluoro-phenoxy)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid benzylamide (0.071 g, 51% yield) as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with brine (2×50 mL)
dry with materialThe organic phase was dried (Na2SO4)
customevaporated
customThe residue was purified by preparative thin layer chromatography over silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record: ord-5551365bbfcc4dc997e8a87f490abec7
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314138B2

Reaction notes

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