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

HRID 1844186Notes

Reaction equation

Cl.Cl[CH2:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][N:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:17][C:18]1[C:19]2[N:20]([C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=2)[CH:21]=[C:22]([CH3:24])[CH:23]=1>CN(C=O)C>[F:10][C:9]1[C:4]([CH2:3][O:17][C:18]2[C:19]3[N:20]([C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:26]([CH3:28])[N:27]=3)[CH:21]=[C:22]([CH3:24])[CH:23]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

15.78 g (86.7 mmol) of 2-(chloromethyl)-3-fluoropyridine hydrochloride (commercially available; additionally described in: U.S. Pat. No. 5,593,993 A1, 1997; WO2007/2181 A2, 2007) and 94.06 g (288.9 mmol) of caesium carbonate were added to 16.92 g (72.2 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 87A in 956 ml of DMF. The reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled to RT and filtered, the filtercake was washed with ethyl acetate and the filtrate was concentrated. About 500 ml of water were added to the residue and the precipitated solid was filtered off and dried under high vacuum. This gave 24.1 g (93% of theory) of the target compound.

Workup

temperatureThe reaction mixture was cooled to RT
filtrationfiltered
washthe filtercake was washed with ethyl acetate
concentrationthe filtrate was concentrated
additionAbout 500 ml of water were added to the residue
filtrationthe precipitated solid was filtered off
customdried under high vacuum

Sources & evidence

ORD record: ord-36e3aa79bf064e73a81448d376572306
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946215B2

Reaction notes

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