Dimethylacetamide → 1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 389110노트

반응식

HRID 389110 반응식
C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.Br[C:23]1[CH:24]=[C:25]2[CH:31]=[CH:30][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:26]2=[N:27][CH:28]=1.C[C:41]([N:43](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn]>[CH3:37][Si:36]([CH3:39])([CH3:38])[CH2:35][CH2:34][O:33][CH2:32][N:29]1[C:26]2=[N:27][CH:28]=[C:23]([C:41]#[N:43])[CH:24]=[C:25]2[CH:31]=[CH:30]1

참가 물질

6

반응물 3

HCID 31374DimethylacetamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 598250161H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-

생성물 1

HCID 582437901-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매

실험 절차

Zinc cyanide (900 mg), biphenyl-2-yl(di-tert-butyl)phosphine (610 mg) and zinc (67 mg) were added to a solution of 5-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (1.917 g) in DMA (25 ml), followed by stirring for 5 minutes while degassing under ice cooling, and palladium (II) trifluoroacetate (338 mg) was added thereto, followed by stirring at 80° C. overnight after making it under an argon atmosphere. Ethyl acetate was added thereto, an insoluble substance was separated by celite filtration, and water was added to the filtrate, followed by extraction. The organic layer was washed with a 3M aqueous ammonia solution and then saturated brine in this order and was dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100 to 0:100) to obtain, as a colorless amorphous solid, 1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (377 mg).

후처리

  1. customwhile degassing under ice cooling
  2. additionpalladium (II) trifluoroacetate (338 mg) was added
  3. stirringby stirring at 80° C. overnight
  4. additionEthyl acetate was added
  5. customan insoluble substance was separated by celite filtration, and water
  6. additionwas added to the filtrate
  7. extractionfollowed by extraction
  8. washThe organic layer was washed with a 3M aqueous ammonia solution
  9. dry with materialsaturated brine in this order and was dried over anhydrous sodium sulfate
  10. customthe solvent was then evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100 to 0:100)

출처 및 근거

ORD 기록
ord-eda98cefadc54d45bcb623578f93350d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377923B2

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