Methanol → HCID 19104978, compound

Participants

Reaction Steps

A mixture of 1,3-dihydro-1-(4-chlorophenyl)-3-(4-pyridinylmethyl)-2H-pyrrolo[2,3-b]pyridin-2-one (3.0 g, 8.93 mmol) and 20 ml 1N NaOH was treated with enough MeOH to effect solution. The mixture was treated dropwise with 3-picolyl chloride hydrochloride (1.6 g, 9.82 mmol) in 10 ml water. The mixture was stirred at room temperature for 2 h, and treated with an additional 20 ml IN NaOH. The mixture was stirred at room temperature for 24 h and concentrated in vacuo. The residue was partitioned between 200 ml CH2Cl2, washed with brine, dried over MgSO4, filtered, and treated with 20 ml 1N HCl/Et2O. The resulting precipitate was collected by filtration, washed with ether, and dried to give the desired product in 90% (4.0 g) yield; mp 208°-211° C., dec.; IR(nujol): 1720 cm-1 (CO); 1H NMR(DMSOd6TMS): d 3.65 [m, 2H, CH2 -(3-Pyr)], 3.71-3.91 [q, 2H, CH2 -(4-Pyr)], [7.06 (d, 2H), 7.22 (m, 1H), 7.53 (d, 2H), 7.60 (d, 2H), 7.85 (dd, 1H), 8.04 (dd, 2H), 8.22 (d, 1H), 8.52 (s, 1H), 8.84 (d, 3H), Ar]; mass spec m/e 427 (M+1).

Provenance & Evidence