Hydrochloric Acid → HCID 136360163, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask containing (2-hydroxyphenyl)boronic acid (1.37 g, 9.9 mmol) in 1,4-dioxane:water (8:1, 40 ml) was added methyl 6-chloronicotinate (1.71 g, 10.0 mmol), potassium carbonate (4.14 g, 30.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.26 mmol) and the resulting mixture stirred at 80° C. for 10 h, then stood at r.t. for 72 h. The solution was acidified to pH 1 with aqueous 2 N HCl and concentrated in vacuo to a volume of approximately 5 ml. This solution was then partitioned between saturated sodium hydrogen carbonate (30 ml) and dichloromethane:methanol (95:5, 150 ml). The layers were separated and the aqueous layer extracted with dichloromethane (50 ml). The organic layers were combined and dried with anhydrous MgSO4, filtered and concentrated to afford a yellow solid. The solid was recrystallised from ethyl acetate/methanol to give the title compound as a yellow solid (1.14 g) (50%). 1H NMR (400 MHz, CDCl3) □ ppm 9.16 (1H, s), 8.46-8.40 (1H, m), 8.02-7.96 (1H, m ), 7.86-7.80 (1H, m), 7.39-7.33 (1H, m), 7.10-7.04 (1H, m), 6.96-6.90 (1H, m), 4.00 (3H, s). LRMS: AP m/z 230 [M+H]+.

Provenance & Evidence