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

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

Reactant 2

HCID 545327tert-Butyl 2-bromopropanoate

HCID 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

customAfter removal of the DMF
customthe desired product was precipitated with water
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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

Loading…