Water → 1H-Pyrrolo[2,3-B]pyridine-3-carbonitrile, 4-chloro-1-(phenylsulfonyl)-

HRID 1696194노트

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HRID 1696194 반응식
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[Cl:11])[N:4]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:3]=1.O.[CH3:22][N:23]1CCN(C)C1=O>[C-]#N.[C-]#N.[Zn+2].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>[Cl:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[N:4]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:3]=[C:2]([C:22]#[N:23])[C:10]=12

참가 물질

6

반응물 3

HCID 962WaterHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 497589583-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

생성물 1

HCID 497590871H-Pyrrolo[2,3-B]pyridine-3-carbonitrile, 4-chloro-1-(phenylsulfonyl)-

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
140 °C

실험 절차

To the solution of 3-bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine in 1,3-dimethyl-2-imidazolidinone was added Zn(CN)2 and tetrakis(triphenylphosphine)palladium(0) at ambient temperature. This was stirred at 140° C. for 1.5 hours. The reaction was cooled and was added water, extracted with EtOAc. The organic layer was washed with brine and was dried over MgSO4 and evaporated. Resultings were purified by silica gel column chromatography to afford 4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile as white powder.

후처리

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialwas dried over MgSO4
  5. customevaporated
  6. customResultings were purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2f332b3486724ce5b0e8f4db3db2eb18
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163767B2

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