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

HRID 884910ノート

反応式

HRID 884910 の反応式
[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

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 1363312684-[5-(Trifluoromethyl)benzoxazole-2-yl]pyridin-3-ol

生成物 1

HCID 668802202-(3-Cyclopentyloxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole収率 83.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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”).

後処理

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

出典と根拠

ORDレコード
ord-82f6d84fa98e4abdaaf292cf4423a8cf
出典データセット
uspto-grants-2012_08
特許番号
US08242133B2

反応ノート

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