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

HRID 1888506Notes

Reaction equation

HRID 1888506 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:27]#[N:28])=[C:18](OS(C(F)(F)F)(=O)=O)[C:13]=3[C:12]3[CH:29]=[CH:30][CH:31]=[N:32][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC.[Cl-].[Li+]>O1CCOCC1.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>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:27]#[N:28])=[C:18]([CH:33]=[CH2:34])[C:13]=3[C:12]3[CH:29]=[CH:30][CH:31]=[N:32][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 58266643HCID 58266643, compound

Product 1

HCID 582665259-Benzenesulfonyl-5-vinyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileYield 53.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of trifluoromethanesulfonic acid 9-benzenesulfonyl-6-cyano-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-yl ester (150 mg, 0.31 mmol), tributyl(vinyl)stannane (102 μL, 0.35 mmol), lithium chloride (40 mg, 0.93 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.0 mg, 6.0 μmol) in dioxane (1.5 mL) was degassed with argon and heated under reflux for 18 h. The reaction mixture was allowed to cool to ambient temperature then diluted with DCM (9 mL) and methanol (1 mL). The resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, 0-2% MeOH in DCM) and triturated with pentane (2×2 mL) to afford the title compound as a white solid (60 mg, 52%). LCMS (Method B): RT=3.73 min, M+H+=361.

Workup

  1. customwas degassed with argon
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. additionthen diluted with DCM (9 mL) and methanol (1 mL)
  5. customThe resultant residue was purified by chromatography (silica, 2 g column, Si-SPE, 0-2% MeOH in DCM)
  6. customtriturated with pentane (2×2 mL)

Sources & evidence

ORD record
ord-1690dfa08cae43748e2bd8271985576f
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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