Hydrochloric Acid → HCID 19104981, compound

Participants

Reaction Steps

The solution 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 75 ml dry THF was treated with NaH (0.26 g, 10.7 mmol) and stirred at room temperature for min. The mixture was then treated dropwise with a solution of a-bromo-m-tolunitrile (1.93 g, 9.82 mmol) dissolved in 25 ml dry THF. The mixture was stirred at room temperature under dry nitrogen for 24 h and concentrated in vacuo. The residue was partitioned between 150 ml CH2Cl2 and 100 ml water. The organic layer was washed with additional water then brine, dried over anh. MgSO4, filtered, and concentrated to a foam. The foam was dissolved in a minimum amount of MeOH and chromatographed on silica gel using CHCl3 --MeOH (95:5) as mobile phase. The appropriate fractions were combined, concentrated in vacuo to 25 ml, and treated with 1N HCl--Et2O (10 ml). The resulting gummy mixture was concentrated to a foam which was triturated with Et2O, collected by filtration, washed with additional Et2O, and dried to give the desire product in 87% (3.8 g) yield as a foam; IR(nujol): 2229 (CN), 1723 (CO) cm-1 ; 1H NMR(DMSOd6TMS): d 3.4-3.6(dd, 2H, CH2 -Phe), 3.6-3.85 (dd, 2H, CH2 -Pyr), [6.91 (d, 2H), 7.25 (m, 3H), 7.61 (m, 3H), Phe-Cl and Phe-CN], [7.37 (dd, 1H), 7.96 (d, 1H), 8.20 (d, 1H), 2,3-Pyr], [7.51 (d, 2H), 8.71 (d, 2H), 1,4-Pyr]; mass spec m/e 451 (M+1). Anal calcd for C27H19N4OCl HCl, MW 487.39: C, 66.54; H, 4.14; N, 11.50. Found:

Provenance & Evidence