Cesium carbonate → HCID 58020014, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(3-bromo-4-methoxy-benzyl)-1H-imidazole (I-167, 267 mg, 1.00 mmol), benzo[1,2,5]oxadiazole-5-boronic acid (I-105, 164 mg, 1.00 mmol), palladium(0)bis(dibenzylideneacetone) (28.7 mg, 0.050 mmol), and triphenylphosphine (26.2 mg, 0.10 mmol) in dimethylformamide (20 mL) and 1 M aqueous cesium carbonate (3.0 mL, 3.0 mmol) was heated to 85° C. with stirring overnight. The solvent was removed under vacuum and the residue suspended in ethyl acetate (25 mL). The organic suspension was washed with water (3×20 mL) and brine, dried over sodium sulfate, decolorized over activated carbon, filtered, and concentrated under. The residue was purified by silica gel preparatory thin layer chromatography (ethyl acetate:dichloromethane 3:1) to give 10.4 mg of P-006 in 9.1% yield. 1H NMR (400 MHz, CDCl3) 3.86 (s, 3H) 5.13 (s, 2H) 6.93 (s, 1H) 7.01 (d, J=8.32 Hz, 1H) 7.10 (s, 1H) 7.17-7.25 (m, 2H) 7.52-7.62 (m, 2H) 7.78-7.85 (m, 2H) ppm. LCMS=100% purity. APCI (+)=307.1 (M+1).

Provenance & Evidence