Dimethylformamide → 1-(2-Hydroxy-ethyl)-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole-5-carbonitrile

HRID 1661947ノート

反応式

HRID 1661947 の反応式
Br[C:2]1[CH:23]=[C:22]([O:24][CH3:25])[C:5]2[N:6]([CH2:18][CH2:19][O:20]C)[C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[CH3:26][N:27](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:20][CH2:19][CH2:18][N:6]1[C:5]2[C:22]([O:24][CH3:25])=[CH:23][C:2]([C:26]#[N:27])=[CH:3][C:4]=2[N:8]=[C:7]1[C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:16])[CH3:17])=[CH:13][CH:14]=1

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 113841195-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

生成物 1

HCID 674309111-(2-Hydroxy-ethyl)-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole-5-carbonitrile

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
180 °C

実験手順

A solution of 1.42 g (3.52 mmol) of 5-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole and 455 mg (3.87 mmol) zinc cyanide in 15 ml DMF is stirred under argon for 10 min at RT. Tetrakis(triphenylphosphine)palladium (214 mg, 0.176 mmol) is added and the reaction is heated to 180° C. for 90 min. After cooling to RT, ice/water is added and the reaction mixture is extracted with ethyl acetate (3×). The organic layer is washed with water, dried (Na2SO4) and concentrated in vacuo and the material is used without further purification.

後処理

  1. temperatureAfter cooling to RT
  2. extractionthe reaction mixture is extracted with ethyl acetate (3×)
  3. washThe organic layer is washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customthe material is used without further purification

出典と根拠

ORDレコード
ord-35ebe1f0b957477890ce768ee7e9d952
出典データセット
uspto-grants-2011_10
特許番号
US08030497B2

反応ノート

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