Dimethylformamide → 2-(3-Cyclopentyloxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole

HRID 884910Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[OH:17])=[N:8][C:7]=2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:32]1(Br)[CH2:36][CH2:35][CH2:34][CH2:33]1>O>[CH:32]1([O:17][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:11]=2[C:9]2[O:10][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:18][C:7]=3[N:8]=2)[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 0.28 g of 4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridin-3-ol, 0.28 g of potassium carbonate and 2 ml of DMF, a mixture of 0.29 g of cyclopentyl bromide and 2 ml of DMF was added at room temperature. The reaction mixture was stirred while heating at 60° C. for four hours. The reaction mixture was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.29 g of 2-(3-cyclopentyloxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 115”).

Workup

additionwas added at room temperature
temperatureThe reaction mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate twice
washThe combined organic layers were washed with water
dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-82f6d84fa98e4abdaaf292cf4423a8cf
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242133B2

Reaction notes

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