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

HRID 1913671노트

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HRID 1913671 반응식
[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

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 1363312684-[5-(Trifluoromethyl)benzoxazole-2-yl]pyridin-3-ol

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

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”).

후처리

  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

출처 및 근거

ORD 기록
ord-6ba03f1821ac4b9aa8bc2a75d6dac585
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609705B2

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