tert-Butyl 2-bromopropanoate → tert-Butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)propanoate

HRID 56627

Reaction equation

HRID 56627 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.Br[CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4](=[O:8])[CH:3]=1

Participants

3

Reactant 2

HCID 545327tert-Butyl 2-bromopropanoateHCID 8171154-Bromo-2-hydroxypyridine

Product 1

HCID 117622807tert-Butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)propanoate

Procedure

6.0 g (34.5 mmol) of 4-bromopyridin-2(1H)-one and 7.9 g (37.9 mmol) of tert-butyl 2-bromopropanoate (racemate) were reacted according to General Method 4B. After removal of the DMF, the desired product was precipitated with water and then purified further by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures). Yield: 7.4 g (69% of theory)

Workup

  1. customAfter removal of the DMF
  2. customthe desired product was precipitated with water
  3. custompurified further by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-a3d9a6c70f324a2bbe12ad35708693af
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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