Cesium carbonate → Ethyl 8-[(3,3-difluorocyclobutyl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1624116Notes

Reaction equation

[OH:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.CS(O[CH2:23][CH:24]1[CH2:27][C:26]([F:29])([F:28])[CH2:25]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:28][C:26]1([F:29])[CH2:27][CH:24]([CH2:23][O:1][C:2]2[C:3]3[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH2:25]1

Participants

Conditions

Temperature: 60 °C

Procedure

1.85 g (7.89 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 87A and 2.37 g (9.47 mmol) of (3,3-difluorocyclobutyl)methyl methanesulphonate Example 105A were initially charged in 104 ml of DMF, and 10.28 g (31.56 mmol) of caesium carbonate were added. The reaction mixture was stirred at 60° C. overnight. After cooling, the reaction mixture was filtered, the solid was washed thoroughly with ethyl acetate, the filtrate was concentrated and about 150 ml of water were added to the residue. The solid formed was filtered off and dried under high vacuum. This gave 2.51 g (89% of theory; purity 95%) of the title compound.

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered
washthe solid was washed thoroughly with ethyl acetate
concentrationthe filtrate was concentrated
additionabout 150 ml of water were added to the residue
customThe solid formed
filtrationwas filtered off
customdried under high vacuum

Sources & evidence

ORD record: ord-a007214b12864819b0964ec3d700f631
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778964B2

Reaction notes

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