9-Benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile → 9-Benzenesulfonyl-5-ethyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1888507Notes

Reaction equation

HRID 1888507 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:21]#[N:22])=[C:18]([CH:19]=[CH2:20])[C:13]=3[C:12]3[CH:23]=[CH:24][CH:25]=[N:26][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C1COCC1>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:21]#[N:22])=[C:18]([CH2:19][CH3:20])[C:13]=3[C:12]3[CH:23]=[CH:24][CH:25]=[N:26][C:11]2=3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 582665259-Benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 582663179-Benzenesulfonyl-5-ethyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileYield 103.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9-benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (60 mg 0.16 mmol) and 10% palladium on carbon (20 mg) in THF (4 mL) and IMS (3 mL) was stirred under an atmosphere of hydrogen for 3 h. The reaction vessel was then purged with nitrogen then the reaction mixture was filtered through celite. The celite pad was washed with DCM and then ethyl acetate and the combined filtrate was concentrated in vacuo to yield the title compound as a beige solid (60 mg, 99%). LCMS (Method B): RT=3.78 min, M+H+=363.

Workup

  1. customThe reaction vessel was then purged with nitrogen
  2. filtrationthe reaction mixture was filtered through celite
  3. washThe celite pad was washed with DCM
  4. concentrationethyl acetate and the combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cd321dad5acf43d5ae93fc2b86e26ec1
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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