Methanol → HCID 66869085、化合物

HRID 250744ノート

反応式

HRID 250744 の反応式
[CH2:1]([N:8]1[C:12](Br)=[CH:11][N:10]=[C:9]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CO>CC([O-])=O.CC([O-])=O.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+2].COCCOC>[CH2:1]([N:8]1[C:12]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][C:20]=2[F:22])=[CH:11][N:10]=[C:9]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 668687951-Benzyl-2-methyl-5-bromo-1H-imidazole

生成物 1

HCID 66869085HCID 66869085、化合物収率 67.4%

試薬・触媒・溶媒 2

HCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Heat a mixture of 1-benzyl-2-methyl-5-bromo-1H-imidazole (4.71 g, 18.7 mmol), 2,4-difluorophenyl boronic acid (6.92 g, 43.8 mmol), bis(acetato)bis(triphenylphosphine)palladium(II) (1.4 g, 1.875 mmol), 2M sodium carbonate (19 mL, 38 mmol), methanol (19 mL) and 1,2-dimethoxyethane (120 mL) to reflux for 18 hours. Cool to room temperature. Add water and ethyl acetate and separate layers. Dry organic layer over magnesium sulfate, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with ethyl acetate/dichloromethane mixtures to give 3.59 g (12.6 mmol) of the desired compound.

後処理

  1. temperatureHeat
  2. temperatureto reflux for 18 hours
  3. customAdd water and ethyl acetate and separate layers
  4. filtrationDry organic layer over magnesium sulfate, filter
  5. concentrationconcentrate under reduced pressure
  6. washSubject residue to silica gel chromatography, eluting with ethyl acetate/dichloromethane

出典と根拠

ORDレコード
ord-4dbd5cf5c4a7483c9599d0d9d0e461b4
出典データセット
uspto-grants-2011_01
特許番号
US07863310B2

反応ノート

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