Dimethylformamide → HCID 18779757, compound

HRID 1421704Notes

Reaction equation

HRID 1421704 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
  6. customThe residue was chromatographed
  7. wash(silica gel, EtOAc: CH2Cl2 10:90 to 12:88 gradient elution)

Sources & evidence

ORD record
ord-98a5b2d3cad84eec965574c5e203dbf6
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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