Benzoyl chloride → Methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate

HRID 1802183ノート

反応式

HRID 1802183 の反応式
C[C:2]1[CH:7]=[C:6](C)[CH:5]=[C:4]([CH3:9])[C:3]=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[C:19]([F:21])[C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]=1[NH2:26].C(Cl)(=O)C1C=CC=CC=1>N1C=CC=CC=1>[F:21][C:19]1[C:18]([C:22]([O:24][CH3:25])=[O:23])=[CH:17][C:16]2[N:15]([N:14]=[C:9]([C:4]3[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=3)[N:26]=2)[CH:20]=1

参加物

4

反応物 2

HCID 7412Benzoyl chlorideHCID 866660181,2-Diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate

生成物 1

HCID 67776717Methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate収率 49.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1,2-diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate (1.719 g, 4.46 mmol) and benzoyl chloride (1.03 ml, 8.92 mmol) in pyridine (12 ml) is stirred for 20 hours at 100° C. The solvent is evaporated and the residue stirred for 2.5 hours with sat. aqueous ammoniumchloride solution while neutralizing to pH 6-7 with sat. aqueous sodium bicarbonate solution. The solid is collected by filtration, washed with water and dried affording methyl 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (603 mg, 49.8%) as a light brown solid. Mp.: 162-8° C. MS: m/z=272.2 (M+H+).

後処理

  1. customThe solvent is evaporated
  2. stirringthe residue stirred for 2.5 hours with sat. aqueous ammoniumchloride solution
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried

出典と根拠

ORDレコード
ord-6d8b2ad8f8de4a489de97708bd04c9ff
出典データセット
uspto-grants-2013_01
特許番号
US08349824B2

反応ノート

読み込み中…