Dimethylformamide → HCID 59467884, compound

Participants

Reaction Steps

Compound 68 (0.5 g, 3.0 mmol) was mixed with 20 mL of dry THF and 20 mL of dry DMF under N2 and the suspension was stirred for 30 min at RT and then cooled to 0° C. NaH (0.15 g 60% in mineral oil, 3.7 mmol) was added to the ice-cold suspension which became a greenish solution upon stirring for several minutes at 0° C. The reaction mixture was stirred for another 30 min at 0° C. and then 2-chloro-1-(3,4-dihydroquinolin-1(2H)-yl)ethanone (0.63 g, 3.0 mmol) dissolved in 5 ml of dry THF was added. After the reaction mixture was stirred for 16 h at RT (monitored by TLC (CH2Cl2/EtOAc=1:1 and MS), it was diluted with 100 mL of EtOAc followed by addition of 50 mL of H2O. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organic layers were combined washed with water, brine, dried over Na2SO4 and concentrated giving 1.1 g of crude which was purified by flash chromatography (CH2Cl2/EtOAc) to yield compound 69 (0.5 g, 49%). MS: m/z+ 342.1 [M+H]+; Anal. Calcd (found) for C17H15N3OS2: C, 59.80 (59.89); H, 4.43 (4.51); N, 12.31 (12.12); S, 18.78 (18.53).

Provenance & Evidence