3-(Chloromethyl)pyridine hydrochloride → HCID 54305681, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 45 (102 mg) in DMF (3 mL) was added Cs2 CO3 (390 mg) and a solution of 3-picolylchloride hydrochloride (154 mg) in DMF (3 mL). The mixture was heated at 80° C. for 18 hr, diluted with EtOAc and H2O. The aqueous phase was extracted with EtOAc, the combined organic phase was washed with brine, dried (MgSO4) and the solvent evaporated. The resulting residue was purified by flash chromatography (silica gel; hexane/EtOAc (40:60)) to give the title compound as white foam; 1H NMR (300 MHz, Ace-d6): δ 1.61 (s,6H), 3.17 (s, 3H), 5.22 (s, 2H), 7.36-7.41 (m, 4H), 7.69 (m, 2H), 7.85 (m, 3H), 7.98 (d, 2H), 8.52 (dd, 1H), 8.68 (br s, 1H).

Provenance & Evidence