Dimethylformamide → HCID 67284590、化合物

HRID 1618654ノート

反応式

HRID 1618654 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.[C:16]1([C:22](B2OC(C)(C)C(C)(C)O2)=[CH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[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]([C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH2:23])[C:11]=1[CH3:12]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 110316711-Phenylvinylboronic acid, pinacol esterHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

生成物 1

HCID 67284590HCID 67284590、化合物

試薬・触媒・溶媒 2

HCID 178478230HCID 178478230、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

A screw cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (99 mg, 0.398 mmol), 1-phenylvinylboronic acid pinacol ester (110 mg, 0.478 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) (32.5 mg, 0.040 mmol), potassium carbonate (165 mg, 1.195 mmol), and DMF (3.98 mL), and the mixture was heated at 95° C. under a N2 atmosphere for 18 h. The reaction was then cooled to rt, diluted with EtOAc, and washed with water and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with a gradient of 0-10% EtOAc in hexane to give 4-chloro-5,7-difluoro-3-methyl-2-(1-phenylvinyl)-quinoline as an orange solid. Mass Spectrum (ESI) m/e=316.0 (M+1).

後処理

  1. customA screw cap vial
  2. temperatureThe reaction was then cooled to rt
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography
  7. washeluting with a gradient of 0-10% EtOAc in hexane

出典と根拠

ORDレコード
ord-ffb918cefec943de9da1394f4ca252c6
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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