ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate → HCID 20158234, compound
Reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)(=O)C.[Rh]>[NH:1]1[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate (4.225 g, 22.21 mmol) was dissolved in acetic acid (150 mL) and 5% Rh/Al2O3 (9.144 g, 0.2 eq.) was added. The suspension was hydrogenated (45 Bars) at rt for 4 days then at 50° C. for 7 days. The catalyst was removed by filtration through a Celite pad, was washed with acetic acid and the filtrate was evaporated. The residue was dissolved in DCM, washed with saturated aqueous solution of NaHCO3 and aqueous phases were extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the title compound (4.183 g, 97%). HPLC purity: 92%. M+(LC-MS (ESI)): 195, M−(LC-MS (ESI)): 193