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

HRID 2094428

反応式

HRID 2094428 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.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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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”).

後処理

  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

出典と根拠

ORDレコード
ord-01f8da89aa7c4173ba32f2ef38f20842
出典データセット
uspto-grants-2013_05
特許番号
US08445522B2

関連ノート

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