Sodium Bicarbonate → HCID 66589882, compound

Participants

Reaction Steps

Into a 20 mL microwave vial was added 4G (1.33 g, 2.05 mmol) and 4-hydroxyphenyl boronic acid (425 mg, 3.1 mmol, 1.5 eq). Dioxane (12 mL) and saturated sodium bicarbonate (4 mL) was added and the mixture was degassed by bubbling N2 through the solution for 10 minutes. After degassing, 1,1′-bis-diphenyl phosphinoferrocene dichloro palladium (II) (Pd(dppf)Cl2) (150 mg, 206 μmol, 0.05 eq) was added and the reaction was capped. The reaction was microwaved at 150° C. for 20 minutes, and the reaction was transferred to a round bottom and the solvent was removed under vacuum. Saturated ammonium chloride (25 mL) and ethyl acetate (25 mL) was added to the residue and transferred to a separatory funnel. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2×25 mL). The organic layers were combined and dried over sodium sulfate. Solution was filtered and the solvent was removed under vacuum. The residue was purified by column chromatography (40% ethyl acetate/hexanes) to give 4H (948 mg, 37%). ESI-MS:m/z 591.3 (M+H)+.

Provenance & Evidence