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

HRID 1696194ノート

反応式

HRID 1696194 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

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
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2f332b3486724ce5b0e8f4db3db2eb18
出典データセット
uspto-grants-2012_04
特許番号
US08163767B2

反応ノート

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