Sodium Bicarbonate → Ethyl imidazo[1,5-a]pyridine-8-carboxylate
Reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[C:15]([O-])(O)=O.[Na+]>>[CH:3]1[N:2]=[CH:15][N:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]=12Participants
3
Procedure
A mixture of 44.8 mL of acetic anhydride and 19.2 mL of formic acid was heated in a 50-60° C. oil bath temperature for 3 h and then cooled to rt to give formic-acetic anhydride, which was then slowly added to the solid ethyl 2-(aminomethyl)-3-pyridinecarboxylate HCl and then stirred at rt for 8 h. Excess reagent was evaporated to give a residue, which was neutralized by very slow addition of sat. NaHCO3 solution. Solution was extracted with DCM, dried and evaporated to provide ethyl imidazo[1,5-a]pyridine-8-carboxylate as a yellow solid (crude weight 2.7 g). MS: exact mass calculated for C10H10N2O2, 190.07; m/z found, 191 [M+H]+.
Workup
- customExcess reagent was evaporated
- custom