Ammonia → 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

HRID 1477760Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[Br:6][C:7]1[N:12]=[C:11]([O:13][CH3:14])[C:10]([N:15]([CH2:18][C:19](=O)[CH3:20])[CH:16]=O)=[CH:9][CH:8]=1.C(OCC)(=O)C.N>C(O)(=O)C>[Br:6][C:7]1[N:12]=[C:11]([O:13][CH3:14])[C:10]([N:15]2[CH:18]=[C:19]([CH3:20])[N:5]=[CH:16]2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A suspension of ammonium acetate (267 g) and N-(6-bromo-2-methoxypyridin-3-yl)-N-(2-oxopropyl)formamide (199 g) in glacial acetic acid (400 mL) was stirred at 130° C. for one hour and 10 minutes. The reaction solution was brought back to room temperature. Ethyl acetate and ice water were added to the reaction solution, and the mixture was ice-cooled. Then, concentrated aqueous ammonia (500 mL) was added dropwise and then the organic layer was separated. The resulting organic layer was sequentially washed with water and brine and dried over anhydrous magnesium sulfate. Then, the organic layer was purified by short silica gel column chromatography. The eluted fraction was concentrated. The resulting reside was triturated with ethyl acetate and tert-butyl methyl ether and dried under reduced pressure to obtain 107.7 g of the title compound.

Workup

customwas brought back to room temperature
temperaturecooled
customthe organic layer was separated
washThe resulting organic layer was sequentially washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customThen, the organic layer was purified by short silica gel column chromatography
concentrationThe eluted fraction was concentrated
customThe resulting reside was triturated with ethyl acetate and tert-butyl methyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-d859dd0f12a74576bfa09e76ef61cdc7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403815B2

Reaction notes

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