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

HRID 730426노트

반응식

HRID 730426 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3e12f060d5ba47feacf19fac42fed92f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582651B2

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