m-Anisoyl chloride → 7-Bromo-2-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1802260ノート

反応式

HRID 1802260 の反応式
[NH2:1][N+:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH2:9].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=O>N1C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][N:2]2[N:1]=[C:28]([C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([O:24][CH3:23])[CH:26]=3)[N:9]=[C:3]2[CH:4]=1

参加物

4

反応物 2

HCID 74374m-Anisoyl chlorideHCID 866660161,2-Diamino-4-bromo-pyridinium 2,4,6-trimethyl-benzenesulfonate

生成物 1

HCID 677747487-Bromo-2-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
85 °C

実験手順

To a solution of 1,2-diamino-4-bromo-pyridinium-2,4,6-trimethyl-benzenesulfonate (Example 1, step a) (8 g, 20.7 mmol) in pyridine (50 ml) was added 3-methoxybenzoyl chloride (6 ml, 41.3 mmol). The reaction mixture was heated at 85° C. for 3 h. Volatiles were removed in vacuum, and the resultant residue was diluted with EtOAc (300 ml). The organic layer was washed successively with water (2×250 ml) and brine (100 ml), dried over anhydrous Na2SO4, filtered, and evaporated in vacuum. The crude material thus obtained was purified by column chromatography over silica gel (10-15% EtOAc/hexane) to afford 7-bromo-2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (8 g, quant) as white solid. LC-MS: m/z=303.8 [M+H]+.

後処理

  1. customVolatiles were removed in vacuum
  2. additionthe resultant residue was diluted with EtOAc (300 ml)
  3. washThe organic layer was washed successively with water (2×250 ml) and brine (100 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuum
  7. customThe crude material thus obtained
  8. customwas purified by column chromatography over silica gel (10-15% EtOAc/hexane)

出典と根拠

ORDレコード
ord-6064580fe75546e096bc2e58161eed86
出典データセット
uspto-grants-2013_01
特許番号
US08349824B2

反応ノート

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