Bromoacetone → HCID 86713417, compound

HRID 64409

Reaction equation

[NH2:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.Br[CH2:22][C:23](=O)[CH3:24].C(=O)([O-])O.[Na+]>C(O)C>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][O:12][C:11]1[C:2]2[N:3]([CH:22]=[C:23]([CH3:24])[N:1]=2)[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 2.15 g of methyl 6-amino-5-[(2-fluorobenzyl)oxy]nicotinate in 43 ml of ethanol was added 1.09 ml of bromoacetone, followed by stirring at 80° C. for 4 hours. To the reaction mixture was added 1.09 ml of bromoacetone, followed by stirring at 80° C. for 4 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the solvent was evaporated under reduced pressure, followed by extracting with ethyl acetate and washing with saturated brine. After drying over anhydrous magnesium sulfate and then filtering, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.39 g of methyl 8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-6-carboxylate.

Workup

stirringby stirring at 80° C. for 4 hours
customthe solvent was evaporated under reduced pressure
extractionby extracting with ethyl acetate
washwashing with saturated brine
dry with materialAfter drying over anhydrous magnesium sulfate
filtrationfiltering
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2d92678427e44e14afb990b87d1e5427
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447090B2

Linked notes

Loading…