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

HRID 1505970Notes

Reaction equation

HRID 1505970 reaction equation
[CH2:1]([C:3]1[C:8]2[C:9]3[CH:15]=[CH:14][CH:13]=[N:12][C:10]=3[NH:11][C:7]=2[CH:6]=[N:5][C:4]=1[C:16]#[N:17])[CH3:2].C1C(=O)N([Br:25])C(=O)C1>CN(C=O)C.C(OCC)(=O)C>[Br:25][C:14]1[CH:13]=[N:12][C:10]2[NH:11][C:7]3[CH:6]=[N:5][C:4]([C:16]#[N:17])=[C:3]([CH2:1][CH3:2])[C:8]=3[C:9]=2[CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 582664645-Ethyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 582666243-Bromo-5-ethyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileYield 79.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-ethyl-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (48 mg, 0.21 mmol) in DMF (1 mL) was added NBS (54 mg, 0.30 mmol) then the reaction mixture was stirred for 18 h at ambient temperature. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with saturated aqueous sodium carbonate (10 mL). The aqueous phase was washed with DCM (2×10 mL), the combined organic phase was washed with saturated brine (2×10 mL) and concentrated in vacuo to afford the title compound as a yellow solid (50 mg, 79%). LCMS (Method B): RT=3.34 min, M+H+=301/303.

Workup

  1. washwashed with saturated aqueous sodium carbonate (10 mL)
  2. washThe aqueous phase was washed with DCM (2×10 mL)
  3. washthe combined organic phase was washed with saturated brine (2×10 mL)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b559629e80d45e8a1ccb191775532d1
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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