Ethyl diazoacetate → HCID 71117301, compound

Participants

Reaction Conditions

Reaction Steps

1-(2,2-Dimethylpropyl)-3-methyl-5-[(1E)-prop-1-en-1-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (33-1, 600 mg, 2.3 mmol, 1.0 equiv) was added to anhydrous toluene (4.8 mL). Ethyl diazoacetate (720 μL, 6.9 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 33-1. 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 33-2 as a white solid. MS m/z (M+H): calculated=346.2127; observed=346.2134.

Provenance & Evidence