Dimethylformamide → HCID 67124107, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-6-methyl-1-(phenylmethyl)-1H-pyrazolo[3,4-b]pyridine (3.45 g, 11.42 mmol), dicyanozinc (1.542 g, 13.13 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.523 g, 0.571 mmol), SPhos (0.562 g, 1.370 mmol), DMF(49 mL), and water (0.5 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was heated at 120° C. for 2 hours, and then cooled to room temperature. The contents were concentrated to 50% volume and then 50 mL of 1N NaOH and 50 mL of EtOAc were added. The solids were filtered off. The phases were separated and the aqueous phase extracted with EtOAc (3×50 mL). The combined EtOAc extracts were washed with water (3×50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude product containing SPhos reagent (˜30-40%) was collected as 3.69 g and used without further purification. LCMS E-S (M+H)=249.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.77 (s, 3 H), 5.73 (s, 2 H), 7.08-7.44 (m, 6 H), 8.16 (s, 1 H)

Provenance & Evidence