Methanol → HCID 66869085, 화합물

HRID 729996

반응식

HRID 729996 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 67.5%

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), 2N Na2CO3 (19 mL, 38 mmol), MeOH (19 mL) and 1,2-dimethoxyethane (120 mL) to reflux for 18 h. Cool to RT. Add water and EtOAc and separate the layers. Dry organic layer over MgSO4, filter, and concentrate. Purify the residue (silica gel chromatography, eluting with EtOAc:CH2Cl2 mixtures) to give the desired compound (3.59 g).

후처리

  1. temperatureHeat
  2. temperatureto reflux for 18 h
  3. customAdd water and EtOAc and separate the layers
  4. filtrationDry organic layer over MgSO4, filter
  5. concentrationconcentrate
  6. customPurify
  7. washthe residue (silica gel chromatography, eluting with EtOAc:CH2Cl2 mixtures)

출처 및 근거

ORD 기록
ord-663562bcc74b4a6da309af86daf84192
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582652B2

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