Boron tribromide → HCID 59843047, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2-(4-methoxybenzyl)-6-phenylpyridazin-3(2H)-one (400 mg, 1368 mmol) in DCM (2.5 mL) at 0° C. under nitrogen was added boron tribromide (1294 μl, 13683 μmol) drop-wise over a 1 minute period. More DCM (10 mL) was added to the reaction to create a suspension and ice bath removed. After 3 hours, the reaction was chilled to 0° C. and quenched with methanol (5 mL). The pH was then adjusted to 14 with NaOH (1 M), then adjusted to 7 with HCl (5 M). The aqueous layer was then extracted 3× with 9:1 CHCl3/IPA (50 mL). The combined organics were then dried with sat NH4Cl and MgSO4. The organic was then concentrated onto dry silica (20 g) and purified on silica (40 g) eluting with 20>40% of EtOAc/DCM. Product was isolated as a white solid. MS (ESI pos. ion) calc'd for C17H14N2O2: 278; found 279 (MH+). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.21 (s, 2 H) 6.68-6.77 (m, 2 H) 7.06 (d, J=9.78 Hz, 1H) 7.22 (d, J=8.61 Hz, 2 H) 7.40-7.55 (m, 3 H) 7.89 (dd, J=8.22, 1.37 Hz, 2 H) 8.04 (d, J=9.78 Hz, 1 H) 9.42 (s, 1 H).

Provenance & Evidence