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

HRID 42559노트

반응식

HRID 42559 반응식
[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]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178509481HCID 178509481, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-7f298eeb3f4f4482b7cad256a8bf217b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

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