1,2-Dibromoethane → Methyl 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4,5-dihydroxypyridine-2-carboxylate (348 mg, 2.06 mmol) in DMF (20 mL) is added solid K2CO3 (3.1 g, 22 mmol) and 1,2-dibromoethane (386 μL, 4.5 mmol). The mixture is heated at 115° C. for 2 h. DMF is removed in vacuo, the residue is partitioned between water and EtOAc. The aqueous layer is again extracted with EtOAc. The combined organic layers are dried (MgSO4) and concentrated in vacuo to give a yellow solid for methyl 2,3-dihydro-1,4-dioxino[2,3-c]pyridine-7-carboxylate (348 mg, 86%): 1H NMR (400 MHz, CDCl3) δ 8.29, 7.71, 4.39, 3.99.

Provenance & Evidence