Water → HCID 68107714, compound

HRID 474121Notes

Reaction equation

HRID 474121 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11](Br)=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH3:19][N:20](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Zn].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]([O:5][C:6]([C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([C:19]#[N:20])=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 68108121HCID 68108121, compound

Product 1

HCID 68107714HCID 68107714, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418851HCID 178418851, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-3-nitro-pyridine-2-carboxylic acid tert-butyl ester (888 mg, 2.93 mmol) in DMF (8.8 ml) was added zinc cyanide (206 mg, 1.76 mmol) and zinc dust (2 mg, 0.03 mmol). The mixture was purged with nitrogen (3 times) bis(tri-tert-butylphosphine)palladium(0) (150 mg, 0.293 mmol) was added and the mixture was heated to 80° C. for 4 h. After cooling to 0° C. water was added and the mixture extracted with EtOAc, the combined organic layers were washed with half saturated aq. NaCl, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4) to provide the title compound as beige solid.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture extracted with EtOAc
  4. washthe combined organic layers were washed with half saturated aq. NaCl
  5. dry with materialdried with Na2SO4
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4)

Sources & evidence

ORD record
ord-3f10b9cfd7204fa4b35a36c21aaa2069
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

Loading…