Dichloromethane → N-(cyclopropyl(5-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)methyl)ethanesulfonamide

Participants

Reaction Steps

The mixture of 3-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-benzooxazol-2-one (115 mg, 0.42 mmol), N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)ethane-sulfonamide (133 mg, 0.42 mmol), PdCl2(dppf).CH2Cl2 (34 mg, 0.04 mmol) and Na2CO3 (2 M in water, 0.42 mL, 0.83 mmol) in DMF (6 mL) was heated at 100° C. for 3 h. After concentration, the residue was diluted with DCM, and subsequently filtered to remove insoluble solid. The filtrate was concentrated and purified by flash column (MeOH—CH2Cl2, v/v, 0-4%) to give N-(cyclopropyl(5-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)methyl)ethanesulfonamide (87 mg, 54%); ESI-MS m/z: 388 [M+1]+, Retention time 1.35 min; 1H-NMR (MeOD, 400 MHz) δ 8.80 (1H, d, J=2.0 Hz), 8.62 (1H, d, J=2.0 Hz), 8.20 (1H, t, J=2.0 Hz), 7.54 (1H, d, J=2.4 Hz), 7.50 (1H, dd, J=8.4, 24 Hz), 7.42 (1H, d, J=84 Hz), 3.95 (1H, d, J=8.8 Hz), 3.52 (3H, s), 3.05-2.92 (2H, m), 1.36-1.30 (1H, m), 1.30 (1H, t, J=7.2 Hz), 0.81-0.77 (1H, m), 0.66-0.62 (2H, m), 0.55-0.47 (1H, m)

Provenance & Evidence