Binap, (A+-)- → HCID 59326791, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 2-chloro-3-(4-methoxypiperidin-1-yl)pyridine (25.0 mg, 0.11 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (32.1 mg, 0.132 mmol), Pd2(dba)3 (5.05 mg, 5.51 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (5.15 mg, 8.27 μmol) and sodium 2-methylpropan-2-olate (26.5 mg, 0.276 mmol) in toluene (440 μL) was sparged under argon for 5 min. The mixture was heated to 120° C. in a microwave reactor for 10 min. More phenol (32 mg) was added and the reaction mixture was heated at 120° C. in microwave for another 25 min. After cooling to RT, the mixture was filtered through celite and washed with DCM. The crude product was purified by silica gel chromatography (12 g, 0-50% EtOAc-hexane) to give N-(4-(3-(4-methoxypiperidin-1-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine as off-white solid. MS (ESI, pos. ion) m/z: 433.0 (M+1). IC50 (uM) +++++.

Provenance & Evidence