2,4-Dichloro-5,7-difluoro-3-methylquinoline → 3-((4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)methyl)benzonitrile

HRID 1618664ノート

反応式

HRID 1618664 の反応式
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[Br-].[C:17]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][Zn+])#[N:18]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([CH2:22][C:21]2[CH:20]=[C:19]([CH:26]=[CH:25][CH:24]=2)[C:17]#[N:18])[C:11]=1[CH3:12]

参加物

5

反応物 2

HCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinolineHCID 178509756HCID 178509756、化合物

生成物 1

HCID 672854223-((4-Chloro-5,7-difluoro-3-methylquinolin-2-yl)methyl)benzonitrile

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A screw cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (500 mg, 2.016 mmol), tetrakis(triphenylphosphine)palladium(0) (233 mg, 0.202 mmol), and THF (5.04 mL). The mixture was sparged with N2, then (3-cyanobenzyl)zinc(II) bromide (0.5M in THF, 4.23 mL, 2.116 mmol) was added and the reaction stirred at 60° C. for 2 h. The reaction was then partitioned between EtOAc and water, and the organic layer washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography, eluting with a gradient of 0-15% EtOAc in hexane to give 3-((4-chloro-5,7-difluoro-3-methylquinolin-2-yl)methyl)benzonitrile. Mass Spectrum (ESI) m/e=329.0 (M+1).

後処理

  1. customA screw cap vial
  2. customThe mixture was sparged with N2
  3. customThe reaction was then partitioned between EtOAc and water
  4. washthe organic layer washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography
  8. washeluting with a gradient of 0-15% EtOAc in hexane

出典と根拠

ORDレコード
ord-8cf4396bdee742e890061360a16698de
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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