Methanol → HCID 66869085, 화합물

HRID 250744

반응식

HRID 250744 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 66869085HCID 66869085, 화합물수율 67.4%

시약·촉매·용매 2

HCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4dbd5cf5c4a7483c9599d0d9d0e461b4
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863310B2

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