Methanol → HCID 19104984, compound

Participants

Reaction Steps

A suspension of 1,3-dihydro-1-(4-chlorophenyl)-3-(4-pyridinylmethyl)-2H-pyrrolo[2,3-b]pyridin-2-one (3.0 g, 8.93 mmol) in 20 ml 1N NaOH was treated with enough MeOH to effect solution. The solution was treated dropwise with a solution of 2-picolylchloride hydrochloride (1.6 g, 9.82 mmol) in 10 ml water over 10 min. The mixture was stirred at room temperature for 16 h, and the resulting solid was colledted by filtration, washed with water, and dried. The solid was recrystallized from CHCl3 --C6H12 to give the desired product in 79% (3.0 g) yield : m.p. 193°-195° ; 1H NMR (300 MHz, CDCl3TMS) δ [3.34 (d, J=12, 1H), 3.56 (d, J=12, 1H) CH2 -(2-Pyr)], [3.48 (d, J=14, 1H), 3.78 (d, J=14, 1H) CH 2 -(4-Pyr)], [6.95 (m, 1H), 8.0 (m, 1H), 8.27 (d, J=7, 1H) Pyr], [7.0 (m, 6H), 7.5 (m, 2H) 2-Pyr & 4-Cl-Phe]), [7.42 (d, J=7, 2H), 8.32 (d, J=7, 2H) 4-Pyr]; IR (Nujol) 1732 (C=O) cm-1 ; MS (NH3 -CI) m/e 427(M+1)/100; Analysis calc'd for C25H19N4OCl H2O: C, 67.49; H, 4.76; N, 12.59; found: C, 67.38; H, 5.01; N, 12.34.

Provenance & Evidence