2-[2-(azetidin-1-yl)-2-oxoethyl]-5-hydroxybenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[2-(azetidin-1-yl)-2-oxoethyl]-5-(benzyloxy)benzonitrile (410 mg, 1.34 mmol) was dissolved in ethanol (2 ml) and palladium hydroxide on carbon (20%) (94 mg, 0.134 mmol) added. The mixture was stirred under an atmosphere of hydrogen gas at RT overnight. The mixture was filtered and the filtrate concentrated under reduced pressure. The reside was purified by column chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 0-25% water:acetonitrile+0.05% formic acid to afford the title compound. LC/MS (m/z): 217 (M+H)+. The mixture was filtered the filtrate concentrated under reduced pressure The reside was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol (22 mg, 0.076 mmol) was dissolved in toluene (1 ml) and 2-[2-(azetidin-1-yl)-2-oxoethyl]-5-hydroxybenzonitrile (15 mg, 0.069 mmol), triphenylphosphine (36 mg, 0.139 mmol), and DIAD (27 μl, 0.139 mmol) added and the mixture stirred at RT overnight. The mixture was diluted with ethyl acetate (20 mL), washed with brine (10 ml), dried over MgSO4, filtered and the solvent removed in vacuo. The reside was purified by column chromatography using a Biotage SiO2 cartridge (25 g) using a gradient eluant of 10-100% EtOAc:hexanes to afford the title compound. LC/MS (m/z): 480 (M+H)+. GPR119 Human EC50: 0.32 nM. washed with brine (10 ml) dried over MgSO4 filtered the solvent removed in vacuo The reside was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[2-(azetidin-1-yl)-2-oxoethyl]-5-(benzyloxy)benzonitrile (410 mg, 1.34 mmol) was dissolved in ethanol (2 ml) and palladium hydroxide on carbon (20%) (94 mg, 0.134 mmol) added. The mixture was stirred under an atmosphere of hydrogen gas at RT overnight. The mixture was filtered and the filtrate concentrated under reduced pressure. The reside was purified by column chromatography using a Biotage RP C18 cartridge (30 g) using a gradient eluant of 0-25% water:acetonitrile+0.05% formic acid. to afford the title compound. LC/MS (m/z): 217 (M+H)+. The mixture was filtered the filtrate concentrated under reduced pressure The reside was purified by column chromatography