3-Nitrophenylboronic Acid → HCID 58020025, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(3-Bromo-4-methoxy-benzyl)-1H-benzotriazole (I-106) (477 mg, 1.50 mmol), 3-nitrophenylboronic acid (250 mg, 1.50 mmol), palladium(0) bis(dibenzylideneacetone) (43 mg, 0.075 mmol), and triphenyl phosphine (39 mg, 0.15 mmol) in dimethylformamide (10 mL) and 1 M aqueous sodium carbonate (4.5 mL, 4.5 mmol) was heated to 85° C. with stirring overnight. The solvent was removed under vacuum and the residue suspended in ethyl acetate (20 mL). The organic suspension was washed with water (3×20 mL) and brine, dried over sodium sulfate, decolorized over activated carbon, and the solvent removed under vacuum to give crude material. The residue was purified dissolving in ethyl acetate (5 mL) and adding hexanes (25 mL) until a solid formed. This was repeated 3 times to give P-482 (210 mg, 39% yield). 1H NMR (400 MHz, CDCl3) 1H NMR (400 MHz, CDCl3): 3.82 (s, 3H), 5.86 (s, 2H), 6.98 (d, J=8.2 Hz, 1H), 7.30-7.37 (m, 2H), 7.37-7.52 (m, 3H), 7.52-7.59 (m, 1H), 7.75 (d, J=7.8 Hz, 1H), 8.12 (d, J=8.3 Hz, 1H), 8.18 (dd, J=8.2, 1.2 Hz, 1H), 8.35 (d, J=1.6 Hz, 1H) ppm. LCMS=93.9% purity.

Provenance & Evidence