Ethyl diazoacetate → Ethyl (1R,2R)-2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

1-(2,2-Dimethylpropyl)-5-ethenyl-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (31-2, 636.4 mg, 2.6 mmol, 1.0 equiv) was added to anhydrous toluene (5.5 mL). Ethyl diazoacetate (807 μL, 7.8 mmol, 3.0 equiv) was added and the resulting solution was heated to 100° C. for 18 h. Following this duration, LCMS showed complete consumption of 31-2. The reaction mixture was diluted with ethyl acetate (50 mL) and saturated NaHCO3 (25 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give an orange oil. Purification by normal-phase HPLC (0-40% EtOAc:hexanes) provided 31-3 as a white solid. MS m/z (M+H): calculated=332.1969; observed=332.1971.

Provenance & Evidence