Dimethylformamide → 1-[(4-Fluorophenyl)(phenyl)methyl]-2-formyl-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 730426ノート

反応式

HRID 730426 の反応式
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:27]2[C:31]3=[N:32][C:33]([CH3:37])=[CH:34][C:35]([CH3:36])=[C:30]3[C:29]([C:38]#[N:39])=[CH:28]2)=[CH:22][CH:21]=1.CN(C)[CH:48]=[O:49]>O1CCCC1.O>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:27]2[C:31]3=[N:32][C:33]([CH3:37])=[CH:34][C:35]([CH3:36])=[C:30]3[C:29]([C:38]#[N:39])=[C:28]2[CH:48]=[O:49])=[CH:24][CH:25]=1

参加物

8

反応物 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 8058HexaneHCID 690584651-[(4-Fluorophenyl)(phenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrileHCID 178418339Butyllithium

生成物 1

HCID 867609531-[(4-Fluorophenyl)(phenyl)methyl]-2-formyl-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of diisopropylamine (4.46 ml, 34.0 mmol) in tetrahydrofuran (50 ml) was added a 1.6 N solution of butyllithium in hexane (21.3 ml, 34.0 mmol) at −78° C., and the mixture was stirred at −78° C. for 15 minutes. To the resultant solution was added dropwise 1-[(4-fluorophenyl)(phenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (9.35 g, 26.3 mmol) at −78° C., and the mixture was stirred at −78° C. for 30 minutes. Dimethylformamide (5.26 ml, 68.0 mmol) was added thereto, the resulting mixture was stirred at room temperature for 1.5 hours, poured into iced water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the objective product as a solid material.

後処理

  1. stirringthe mixture was stirred at −78° C. for 30 minutes
  2. stirringthe resulting mixture was stirred at room temperature for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-3e12f060d5ba47feacf19fac42fed92f
出典データセット
uspto-grants-2009_09
特許番号
US07582651B2

反応ノート

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