Dimethylformamide → HCID 18779757, compound

HRID 1585884Notes

Reaction equation

HRID 1585884 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:15])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)[CH:7]=1.[CH3:16][N:17](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:16]([C:2]1[CH:3]=[CH:4][C:5](=[O:15])[N:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)[CH:7]=1)#[N:17]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 18779736HCID 18779736, compound

Product 1

HCID 18779757HCID 18779757, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
95 °C

Procedure

To a suspension of 5-bromo-5'-methyl-[1,2']bipyridinyl-2-one (0.29 g, 1.09 mmol) and zinc cyanide (0.154 g, 1.30 mmol) in degassed DMF (3 ml) was added tetrakis (triphenylphosphine) palladium (151 mg, 0.13 mmol) and the reaction warmed to 95° C. for 4 hrs. The reaction was cooled and quenched with NH4OH (10 ml) and water (30 ml). The aqueous phase was extracted with CH2Cl2, dried (MgSO4), and evaporated in vacuo The residue was chromatographed (silica gel, EtOAc: CH2Cl2 10:90 to 12:88 gradient elution) to afford the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with NH4OH (10 ml) and water (30 ml)
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo The residue
  6. customwas chromatographed
  7. wash(silica gel, EtOAc: CH2Cl2 10:90 to 12:88 gradient elution)

Sources & evidence

ORD record
ord-51dc5e06e63742f78913ee8e75e41dd8
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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