Ammonia → 6-Chloro-2-(4-fluorophenyl)-3,4'-bipyridine-5-carbonitrile

HRID 42559ノート

反応式

HRID 42559 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]#[N:21])=[C:10](O)[N:9]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:25].N>CN(C=O)C>[Cl:25][C:10]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:12][C:11]=1[C:20]#[N:21]

参加物

5

反応物 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178509481HCID 178509481、化合物

生成物 1

HCID 859950346-Chloro-2-(4-fluorophenyl)-3,4'-bipyridine-5-carbonitrile収率 55.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(4-fluorophenyl)-6-hydroxy-3,4′-bipyridine-5-carbonitrile (6.57 g, 22.5 mmol, obtained in reference example 10), POCl3 (26.3 mL, 287.5 mmol) and DMF (0.37 mL) was heated to reflux under argon atmosphere for 2 h. It was cooled with an ice bath and basified by adding 30% aqueous NH3. The precipitate obtained was filtered and washed with water. The product was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 3.86 g of the desired product as a yellow solid (yield: 55%).

後処理

  1. temperaturewas heated
  2. temperatureto reflux under argon atmosphere for 2 h
  3. temperatureIt was cooled with an ice bath
  4. customThe precipitate obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe product was purified by chromatography on silica gel
  8. temperatureof increasing polarity as eluent

出典と根拠

ORDレコード
ord-7f298eeb3f4f4482b7cad256a8bf217b
出典データセット
uspto-grants-2013_09
特許番号
US08536194B2

反応ノート

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