Potassium Hydroxide → HCID 66632518, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-4-(7,8-dimethoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile (540 mg, 1.32 mmol) is dissolved in N,N-dimethylformamide (4.0 ml) under an argon protective-gas atmosphere. Tripotassium phosphate (578 mg, 2.64 mmol), KOH (67 mg, 1.19 mmol), 1,2-dimethoxyethane (9.0 ml) and water (50 μl), vinylboronic acid pinacol ester (942 μl, 5.28 mmol) and trans-bis(tricyclohexylphosphine)palladium(II)dichloride (98 mg, 132 μmol) are subsequently added. The suspension obtained is heated at 150° C. (microwave) for 30 min. For work-up, the mixture is extracted with ethyl acetate and semi-saturated sodium chloride solution. The organic phase is dried over Na2SO4, filtered with suction and evaporated to dryness in vacuo. The residue is purified over flash silica gel (solvent gradient cyclohexane/0-80% by vol. of ethyl acetate), giving 4-(7,8-dimethoxy-3H-pyrazolo[3,4-c]-quinolin-1-yl)-2-vinylbenzonitrile (247 mg, 693 μmol) as a solid. MS: 357.2 (M+H+), TLC (HPTLC): Rf=0.47 (ethyl acetate/ethanol 8:1, parts by volume).

Provenance & Evidence