Water → 6-Pyridin-3-yl-1,3-dihydro-indol-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture 6-chloroindolin-2-one (100 mg, 0.60 mmol), 3-(3,3,4,4-tetramethylborolan-1-yl)pyridine (184 mg, 0.90 mmol), Pd2dba3 (5.4 mg, 0.0060 mmol) and powdered K3PO4 (252 mg, 1.2 mmol) in n-BuOH (2 mL) was degassed by evacuation and refilling with Ar. Dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (11.4 mg, 0.024 mmol) was added under the atmosphere of Ar. The reaction mixture was sealed and heated with stirring under microwave irradiation at 100° C. for 99 min. Later the reaction was cooled to rt and treated with degassed H2O (0.25 mL). The mixture was reheated under microwave irradiation at 110° C. for 1 h. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using MeOH (0 to 6%) in DCM as the eluent to provide the title compound as a pale yellow solid (100 mg, 80%). %). 1H NMR (400 MHz, CD3OD) δ ppm 8.77 (d, J=1.52 Hz, 1H), 8.52 (dd, J4.80, 1.52 Hz, 1H), 8.05-8.10 (m, 1H), 7.52 (dd, J7.33, 4.80 Hz, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.30 (dd, J=7.71, 1.39 Hz, 1H), 7.17 (s, 1H), 3.59 (s, 2H); MS ESI 211.0 (100) [M+H]+, calcd for [C13H10N2O+H]+ 211.2.

Provenance & Evidence