2,6-Lutidine → Ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 923503Notes

Reaction equation

[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.Cl[CH:19]([C:25]([CH3:27])=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].CC1C=CC=C(C)N=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:25]([CH3:27])[N:12]=2)[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 130 °C

Procedure

Under a nitrogen atmosphere, a mixture of 5.0 g of 3-[(2,6-difluorobenzyl)oxy]pyridin-2-amine, 4.1 ml of ethyl 2-chloroacetoacetate, 3.5 ml of 2,6-dimethylpyridine, and 50 ml of toluene was stirred at 130° C. for 24 hours. After leaving to be cooled to room temperature, the reaction mixture was washed with water, a 1 M aqueous sodium hydroxide solution, a 10% aqueous citric acid solution, and a saturated aqueous sodium chloride solution. The organic layer was concentrated under reduced pressure to obtain 5.47 g of ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate.

Workup

customAfter leaving
temperatureto be cooled to room temperature
washthe reaction mixture was washed with water
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-049810546c274661a31b6b73477ade76
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278968B2

Reaction notes

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