Water → 3-Bromo-1-(2,6-dimethyl-4-nitrophenyl)pyridin-2(1H)-one

HRID 452241Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10]([CH3:13])([O-])[CH3:11].[K+].F[C:16]1C=C(C)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=1C.O>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:8])[N:4]([C:9]2[C:17]([CH3:16])=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:11][C:10]=2[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.81 g (16.1 mmol) of 3-bromopyridin-2(1H)-one (O, S. Tee, M. Pavent, J. Am. Chem. Soc. 1982, 104, 4142-4146.) are dissolved in 100 ml of DMF. The mixture is cooled to 0° C., and 2.71 g (24.2 mmol) of potassium tert-butoxide are added. The ice bath is removed, and the mixture is stirred at room temperature for 30 min. 3.00 g (17.7 mmol) of 1-fluoro-2,5-dimethyl-4-nitrobenzene are added, and the mixture is stirred at 80° C. for 18 h, at 100° C. for 36 h and at 120° C. for 18 h. The mixture is then added to water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1). This gives 2.04 g (38% of theory) of the desired compound.

Workup

customThe ice bath is removed
stirringthe mixture is stirred at 80° C. for 18 h, at 100° C. for 36 h and at 120° C. for 18 h
extractionextracted three times with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulphate
customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-49833d23a78d4a14a2bd39d13109444d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487111B2

Reaction notes

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