Methyl 2-aminopyridine-4-carboxylate → Methyl 2-(2,5-difluorophenyl)imidazo[1,2-a]pyridine-7-carboxylate

HRID 60127

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[F:12])=O.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][N:23]=1)[C:17]([O:19][CH3:20])=[O:18]>C(O)C>[F:12][C:6]1[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:5]=1[C:3]1[N:13]=[C:14]2[CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[CH:21]=[CH:22][N:23]2[CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Bromo-1-(2,5-difluorophenyl)ethanone (1.5 g) was added to an ethanol (8.2 ml) solution of methyl 2-aminoisonicotinate (1.0 g), and the obtained mixture was then stirred in a nitrogen atmosphere at 60° C. for 18 hours. Thereafter, 2-bromo-1-(2,5-difluorophenyl)ethanone (0.77 g) was added to the reaction solution, and the obtained mixture was then stirred for 6 hours at the same temperature as described above. Thereafter, the reaction solution was concentrated under reduced pressure, and ethyl acetate (10 ml) was then added to the obtained residue. The precipitated solid was collected by filtration, and it was washed with ethyl acetate (15 ml) and heptane (6 ml) and was then dried, so as to obtain the title compound (2.5 g) in the form of a pink solid.

Workup

stirringthe obtained mixture was then stirred for 6 hours at the same temperature
concentrationThereafter, the reaction solution was concentrated under reduced pressure, and ethyl acetate (10 ml)
additionwas then added to the obtained residue
filtrationThe precipitated solid was collected by filtration, and it
washwas washed with ethyl acetate (15 ml) and heptane (6 ml)
customwas then dried

Sources & evidence

ORD record: ord-1d414470be0b476fab1ac89e737035b4
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440970B2

Linked notes

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