Methanol → HCID 66869085、化合物

HRID 729996

反応式

HRID 729996 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 67.5%

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), 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).

後処理

  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)

出典と根拠

ORDレコード
ord-663562bcc74b4a6da309af86daf84192
出典データセット
uspto-grants-2009_09
特許番号
US07582652B2

関連ノート

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