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

HRID 1618664노트

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HRID 1618664 반응식
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]

참가 물질

5

반응물 2

HCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinolineHCID 178509756HCID 178509756, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8cf4396bdee742e890061360a16698de
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

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