Water → 3-{4-[4-Bromo-3-(trifluoromethyl)phenoxy]phenyl}pyridin-2-amine

HRID 1405930

反応式

HRID 1405930 の反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH2:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1.[Br:23][C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][C:25]=1[C:31]([F:34])([F:33])[F:32].O>CS(C)=O.CCOC(C)=O>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([O:22][C:19]2[CH:20]=[CH:21][C:16]([C:15]3[C:10]([NH2:9])=[N:11][CH:12]=[CH:13][CH:14]=3)=[CH:17][CH:18]=2)=[CH:26][C:25]=1[C:31]([F:32])([F:33])[F:34]

参加物

7

反応物 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 5209832-Bromo-5-fluorobenzotrifluorideHCID 667484774-(2-Aminopyridin-3-yl)phenol

生成物 1

HCID 667486773-{4-[4-Bromo-3-(trifluoromethyl)phenoxy]phenyl}pyridin-2-amine収率 69.2%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

Tripotassium phosphate (3.42 g) was added to a mixture of 4-(2-aminopyridin-3-yl)phenol (1.00 g) and 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (1.57 g) in DMSO (15 mL). The mixture was stirred at 140° C. under nitrogen for 7 hr. Water and EtOAc were added and the extracted organic layer was washed with brine. Silica-gel was added to the organic layer and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) and concentrated to give 3-{4-[4-bromo-3-(trifluoromethyl)phenoxy]phenyl}pyridin-2-amine (1.52 g) as orange oil.

後処理

  1. washthe extracted organic layer was washed with brine
  2. additionSilica-gel was added to the organic layer
  3. customthe volatiles were removed in vacuo
  4. customwas purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e2bd9ac9e8db4e5ebb45b1e01c5b4ef8
出典データセット
uspto-grants-2014_12
特許番号
US08916551B2

関連ノート

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