Propargyl alcohol → HCID 12083033, compound

Participants

Reaction Conditions

Reaction Steps

A solution of palladium acetate (73 mg) and triphenyl phosphine (191 mg) in dry THF (6.0 mL) under nitrogen is cooled to 0° C. A solution of n-butyllithium (1.6 M in hexanes, 444 μL) is added dropwise and after 15 min, the solution is warmed to 22° C. for 15 min. The solution is then canulated into a mixture of ethyl 8-bromo-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate (Preparation 13, 350 mg), copper iodide (84 mg) and propargyl alcohol (75 μL) in diethylamine (6.0 mL). The reaction is warmed to 45° C. for 2 hours. The reaction is filtered, diluted with CH2Cl2 (100 mL), and washed with water. The organic layer is dried (MgSO4), filtered, and concentrated. The crude product is chromatographed over silica gel, eluting with 5% MeOH in CHCl3 and recrystallized from EtOAc to afford 229 mg of the title compound as white crystals. Physical characteristics: M.p. 237° C. (dec); 1H NMR (DMSO-d6) δ8.74, 7.81, 7.60, 5.37, 4.33, 4.23, 3.39, 1.63 (s, 6 H), 1.29 (t, J=7 Hz, 3 H); IR (diffuse reflectance) 2391, 2222, 2058, 1921, 1680, 1637, 1595, 1542, 1510, 1317, 1216, 1186, 1040, 1031, 808 cm−1; MS (EI) m/z 325 (M+). HRMS (FAB) m/z 326.1385 (C19H19NO4+H).

Provenance & Evidence