Tetrahydrofuran → 5-Oxo-6-(pyridine-2-yl)-1,2,3,5-tetrahydroindolizine-8-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-oxo-8-propionyl-1,2,3,5-tetrahydroindolizin-6-yl trifluoromethanesulfonate (0.50 g, 1.46 mmol), 2-trimethylstannyl pyridine (0.46 g, 1.90 mmol), LiCl (0.17 g, 4.38 mmol), and (Ph3P)4Pd (0.12 g, 0.11 mmol) in THF (10 mL) was heated by Microwave Synthesizer at 160° C. for 20 min. The reaction was cooled, diluted with H2O and extracted into EtOAc (3×). The organic layers were combined, dried over MgSO4 and concentrated. The concentrate was triturated in ether to give the salt of the title compound as a light green solid. The solid was dissolved in MeOH (5 mL), to which was added 2 eq. of 1N NaOH and the mixture was stirred for 2 h. The mixture was concentrated, taken up in H2O, neutralized by 10% HCl, extracted with CH2Cl2 (3×), dried over MgSO4, concentrated to give the title compound as a light yellow oil (0.32 g, 85%). MS (m/z, M+1): 257.1.

Provenance & Evidence