Cesium carbonate → HCID 68795331, compound

Participants

Reaction Steps

Synthesis 5-(5-Benzoimidazol-1-ylmethyl-2-methoxy-phenyl)-benzo[1,2,5]oxadiazole (P-014). A suspension of 1-(3-Bromo-4-methoxy-benzyl)-1H-benzoimidazole (I-107, X═N) (250 mg, 0.778 mmol), 1 N aqueous cesium carbonate (2.4 mL), and triphenylphosphine (20.7 mg, 0.0788 mmol) in DMF (5 mL) was stirred. To the suspension was added benzo[1,3]dioxol-5-yl-boronic acid (155 mg, 0.946 mmol), the reaction purged with nitrogen, and bis(dibenzylideneacetone)palladium(0) (22.7 mg, 0.0394 mmol) was added under nitrogen. The reaction was stirred at 100° C. overnight. After cooling to room temperature, ethyl acetate (50 mL) was added. The organic suspension was washed with saturated aqueous ammonium chloride (2×50 mL), 1 N aqueous sodium hydroxide (3×50 mL), water (50 mL), and brine (50 mL), decolorized over activated carbon, dried over sodium sulfate, and removed under vacuum to give crude product. The product was purified by flash silica gel column chromatography eluting with 1% methanol in dichloromethane to give P-014 (102.1 mg, 36% yield) as an off white powder. 1H NMR (400 MHz, d6-DMSO) d: 8.446 (s, 1H), 8.054-8.020 (m, 2H), 7.715 (dd, J=9.60 Hz, 1.60 Hz, 1H), 7.651-7.649 (m, 2H), 7.605 (d, J=2.40 Hz, 1H), 7.440 (dd, J=8.60 Hz, 2.20 Hz, 1H), 7.244-7.147 (m, 3H), 5.485 (s, 2H), 3.787 (s, 3H).

Provenance & Evidence