Formic Acid → HCID 86701124, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 141 (1.6 g, 2.6 mmol) in 1,4-dioxane (20 mL) was added Pd(PPh3)4 (760 mg, 0.6 mmol), triethylamine (664 mg, 6.5 mmol) and formic acid (242 mg, 5.2 mmol) at room temperature under nitrogen atmosphere. The resulting mixture was heated to 60° C. for 20 minutes, and followed by addition of additional formic acid (605 mg, 26 mmol). After stirred overnight at 60° C., removal of volatiles gave a residue, which was dissolved into dichloromethane (50 mL) and neutralized with saturated aqueous NaHCO3 solution (30 mL). The aqueous layer was extracted with dichloromethane (3×30 mL). The combined organic layer was dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography with 20%-30% ethyl acetate in petroleum ether to afford 142 as colorless oil (1.1 g, 77%). (ES, m/z): [M+H]+ 569.0; 1H NMR (300 MHz, CDCl3) δ 7.34-7.23 (m, 10H), 6.17-6.13 (m, 1H), 4.62-4.46 (m, 2H), 4.43-4.00 (m, 4H), 3.91-3.73 (m, 3H), 1.52 (s, 9H).

Provenance & Evidence