Lithium Chloride → HCID 46946832, compound

Participants

Reaction Conditions

Reaction Steps

5,7-Dichloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.40 g, 1.04 mmol), 2-aminopyridine-5-boronic acid pinacol ester (0.28 g, 1.25 mmol) and lithium chloride (0.13 g, 3.1 mmol) were added to 1,4-dioxane (4 mL). Nitrogen was bubbled into solution as reagents were added. Tetrakis(triphenylphosphine) palladium(0) (0.12 g, 0.10 mmol) was added followed by cesium hydroxide monohydrate (0.53 g, 3.1 mmol) and water (1 mL). After bubbling through nitrogen for 5 minutes the reaction was heated to 100° C. for 1 h under a nitrogen atmosphere. The mixture was cooled to ambient temperature, diluted with ethyl acetate (25 mL), washed with water (2×20 mL), brine (20 mL), dried with sodium sulfate, decanted then concentrated in the presence of silica. Chromotography eluting with a gradient of 30-100% ethyl acetate in hexanes provided 5-(6-aminopyridin-3-yl)-7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (140 mg, 30% yield). 1H NMR (300 MHz, d6-DMSO) δ 3.47 (m, 2H) 3.75 (m, 1H), 6.43 (m, 1H), 6.50 (s, 2H), 7.27 (m, 1H), 7.40-7.67 (m, 6H), 7.75-7.82 (m, 4H), 7.92 (m, 1H); ESI m/z measured 441.1487 [M+H]+. calculated 441.1482.

Provenance & Evidence