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

HRID 2190787

반응식

HRID 2190787 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.Cl[CH:33]([F:35])[F:34]>O>[F:34][CH:33]([F:35])[O:17][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:1])[F:20])=[CH:18][C:7]=2[N:8]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 1363312684-[5-(Trifluoromethyl)benzoxazole-2-yl]pyridin-3-ol

생성물 1

HCID 668804752-(3-Difluoromethoxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 0.50 g of 4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridin-3-ol, 1.23 g of potassium carbonate and 14 ml of DMF was stirred while heating at 70° C. for three hours with chlorodifluoromethane gas injected. By stopping injection of gas, the mixture was cooled to room temperature and allowed to stand overnight. 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 0.11 g of 2-(3-difluoromethoxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 126”).

후처리

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe combined organic layers were washed with water
  3. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5a17a6c2bf534551b4620d8c0309e468
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324387B2

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