Acetonitrile → 4-Chloro-7-fluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

HRID 1618541ノート

反応式

HRID 1618541 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:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].O>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=[C:2]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[S:16][CH3:15])[C:11]=1[CH3:12]

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 596311082,4-Dichloro-7-fluoro-3-methylquinoline

生成物 1

HCID 672849044-Chloro-7-fluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2,4-dichloro-7-fluoro-3-methylquinoline (100 mg, 0.44 mmol), 2-(methylthio)phenylboronic acid (95 mg, 0.57 mmol) (in a mixture with the 5-F regioisomer; described herein), tetrakis(triphenylphosphine)palladium(o) (25.1 mg, 0.022 mmol), sodium carbonate (230 mg, 2.17 mmol), acetonitrile (3 mL), and water (1.5 mL) was heated in a microwave at 100° C. for 60 min, then partitioned between EtOAc and water. The organic layer was washed with brine, dried (MgSO4), and concentrated. Column chromatography afforded (in order of elution) 4-chloro-7-fluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline and 4-chloro-5-fluoro-3-methyl-2-(2-(methylthio)phenyl) as white solids. Mass Spectrum (ESI) m/e=318 (M+1).

後処理

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-963a6ef740ea4539a93ada5633e366ff
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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