Dimethylformamide dimethyl acetal → 1-(5-Bromopyridin-3-yl)-3-(dimethylamino)prop-2-ene-1-one

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[Br:9][C:10]1[CH:11]=[C:12]([C:16](=[O:18])[CH3:17])[CH:13]=[N:14][CH:15]=1>>[Br:9][C:10]1[CH:11]=[C:12]([C:16](=[O:18])[CH:17]=[CH:3][N:4]([CH3:5])[CH3:6])[CH:13]=[N:14][CH:15]=1

Participants

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal

HCID 8204233-Acetyl-5-bromopyridine

Product 1

HCID 670572791-(5-Bromopyridin-3-yl)-3-(dimethylamino)prop-2-ene-1-one

Conditions

Temperature: 100 °C

Procedure

An N,N-dimethylformamide dimethylacetal (2 ml) solution containing 1-(5-bromopyridin-3-yl)ethanone (100 mg) (WO2009/87224 A1) was stirred at 100° C. for 5 hours. The solvent was distilled away under reduced pressure, and a yellow solid of 1-(5-bromopyridin-3-yl)-3-(dimethylamino)prop-2-ene-1-one was thus obtained.

Workup

distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record: ord-9ea3052c2c8641589f76c41843130f54
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895585B2

Reaction notes

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