5-Indolylboronic acid → HCID 16755225, compound

Participants

Reaction Steps

A microwave vial containing a stirring bar is loaded with 148 mg (0.5 mmol) of (4SR, 5RS)-(1-aza-bicyclo[3.3.1]non-4-yl)-(5-bromo-pyridin-2-yl)-amine, 98 mg (0.61 mmol) of indole-5-boronic acid and 29.7 mg of tetrakis(triphenylphosphine)palladium, capped and after evacuation purged with argon. After addition of 9 ml of toluene, 1 ml of EtOH and 1 ml of 21 M Na2CO3 soln. the mixture is irradiated at 120° C. for 45 min in a microwave reactor (Initiator Exp, Biotage). The reaction mixture is filtered over hyflo and diluted with AcOEt. The aq. phase is extracted with AcOEt, the combined organic phases are washed with water and brine, dried over Na2 SO4 and evaporated. The residue is purified by medium pressure chromatography on silica gel with AcOEt/MeOH/NEt3 50:45:5 affording a foam which after trituration with pentane yields 73 mg of (4SR,5RS)-(1-aza-bicyclo[3.3.1]non-4-yl)-[5-(1H-indol-5-yl]-pyridin-2-yl)-amine as beige powder. MS (ES+): m/e=333 (MH+).

Provenance & Evidence