反応式
C[N:2](C)[CH2:3][CH2:4]N(C)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.BrC1[CH:57]=[CH:56][C:55]([C:58](=[O:60])[CH3:59])=[CH:54][C:53]=1[F:61]>CN(C)C=O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:58]([C:55]1[CH:56]=[CH:57][C:4]([C:3]#[N:2])=[C:53]([F:61])[CH:54]=1)(=[O:60])[CH3:59]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 160 °C
実験手順
N,N,N′,N′-Tetramethylethylenediamine (0.667 mL, 4.42 mmol), zinc cyanide (1.46 g, 12.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (54.05 mg, 0.059 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (124.3 mg, 0.215 mmol) was added successively to a solution of 1-(4-bromo-3-fluorophenyl)ethanone (4.34 g, 20.0 mmol) in N,N-dimethylformamide (15 mL) in a microwave tube. The tube was sealed and degassed three times, and heated to 160° C. under microwave irradiation with a 240 s hold time, and 300 Watt maximum power input. After cooling, the reaction mixture was filtered through a pad of Celite with a thin layer of silica gel in the middle using dichloromethane as the eluant. The combined filtrates were concentrated under reduced pressure. The residue was purified by chromatography on silica gel with ethyl acetate in hexanes (0-40%) to give the desired product. (3.20 g, 98.1%).
後処理
- customThe tube was sealed
- customdegassed three times
- temperatureAfter cooling
- filtrationthe reaction mixture was filtered through a pad of Celite with a thin layer of silica gel in the middle
- concentrationThe combined filtrates were concentrated under reduced pressure
- customThe residue was purified by chromatography on silica gel with ethyl acetate in hexanes (0-40%)
出典と根拠
- ORDレコード
- ord-77ff4e5b5c7244ae8e31d1c30552ca0c
- 出典データセット
- uspto-grants-2010_08
- 特許番号
- US07767675B2
関連ノート
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