Pyruvic Acid → 6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Pyruvic acid (0.86 mL, 12.4 mmol) was added to a solution of 2-chloro-5-iodo-pyridin-4-ylamine (Preparation 115, 1.05 mg, 4.13 mmol), palladium acetate (56 mg, 0.25 mmol) and DABCO (1.39 g, 12.4 mmol) in anhydrous DMF (30 ml). The reaction mixture was degassed with argon for 20 min, then heated to 145° C. for 2 h. The solvent was removed in vacuo and the residue taken up in water (200 mL). The suspension was made alkaline (pH 9–10) with dilute NaOH solution (1M) and filtered through Celite. After washing of the filtrate with ethyl acetate (50 mL) and ether (50 mL) the pH was adjusted to 3 with dilute HCl solution (1M). Extraction with ethyl acetate (5×50 mL), drying of the combined extracts (MgSO4) and concentration gave the title compound. δH (d6 DMSO): 7.24 (1H, s), 7.42 (1H, s), 8.80 (1H, s); m/z (ES−)=195.02 [M−H]−; RT=2.36 min.

Provenance & Evidence