Cesium carbonate → HCID 58020100, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(3-Bromo-4-methoxy-benzyl)-1H-[1,2,4]triazole (I-104, 402 mg, 1.50 mmol), benzo[1,2,5]oxadiazole-5-boronic acid (I-105, 246 mg, 1.50 mmol), palladium(0) bis(dibenzylideneacetone) (43 mg, 0.075 mmol), and triphenyl phosphine (39.3 mg, 0.15 mmol) in dimethylformamide (15 mL) and 1 M aqueous cesium 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 (15 mL). The organic suspension was washed with water (3×15 mL) and brine, dried over sodium sulfate, decolorized over activated carbon, filtered, and the solvent removed under vacuum to give crude material. The residue was purified by recyrstalization from dichloromethane (2 mL) and hexanes (10 mL) to give P-481 (180 mg, 39% yield). 1H NMR (400 MHz, CDCl3) δ ppm 3.88 (s, 4H) 5.51 (s, 2H) 7.06 (d, J=7.8 Hz, 1H) 7.41-7.54 (m, 3H) 7.59 (d, J=9.3 Hz, 1H) 7.71-8.03 (m, 3H) 8.25 (s, 1H) 9.34 (br. s., 1H), LCMS=95.7% purity.

Provenance & Evidence