4-Bromo-2-hydroxypyridine → tert-Butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)butanoate

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.Br[CH:10]([CH2:18][CH3:19])[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]([CH2:18][CH3:19])[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 8171154-Bromo-2-hydroxypyridine

HCID 13124118tert-Butyl 2-bromobutanoate

Product 1

HCID 117622861tert-Butyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)butanoate

Procedure

348 mg (2.0 mmol) of 4-bromopyridin-2(1H)-one and 1.2 eq. of tert-butyl 2-bromobutanoate (racemate) were reacted according to General Method 4B at 120° C. After aqueous work-up, the desired product was reacted further as crude product. Yield: 608 mg (purity 82%, 79% of theory)

Workup

customaccording to General Method 4B at 120° C

Sources & evidence

ORD record: ord-14b2ea9e819e44e5aba150649ad2e6ec
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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