Ethyl Acetate → Methyl 3-(5-bromopyridin-3-yl)propanoate

HRID 391343Notes

Reaction equation

HRID 391343 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([O-:12])=[O:11])[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+].[C:15](OCC)(=O)C>CO.[Cl-].[Na+].O.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:15][O:11][C:10](=[O:12])[CH2:9][CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 75639055HCID 75639055, compound

Product 1

HCID 59578425Methyl 3-(5-bromopyridin-3-yl)propanoate

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-(5-bromopyridin-3-yl)acrylate (180 mg, 0.744 mmol) and nickel chloride hexahydrate (17.6 mg, 0.074 mmol) in MeOH (3 ml) was added sodium borohydride (56.3 mg, 1.487 mmol) at 0° C. This mixture was stirred for 30 min at room temperature. Brine and ethyl acetate were added and the organic layer was separated and washed with brine twice. The combined organic layer was dried over Na2SO4, filtered and concentrated to give 155 mg of crude 3-(5-Bromo-pyridin-3-yl)-propionic acid methyl ester. ESI-MS m/z: 246[M+1]+.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine twice
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4b2bb34c5d943d59f5df046b00eba52
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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