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

HRID 1696194Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

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.

Workup

temperatureThe reaction was cooled
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialwas dried over MgSO4
customevaporated
customResultings were purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2f332b3486724ce5b0e8f4db3db2eb18
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163767B2

Reaction notes

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