Triethylamine → HCID 89463184, compound

Participants

Reaction Conditions

Reaction Steps

An ice cold solution of methyl 5-(4-fluorobenzyl)-9-hydroxy-7-methyl-6-oxo-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridine-8-carboxylate (2.54 g, 6.57 mmol) and Et3N (4.56 ml, 32.9 mmol) in DCM (40 mL) was treated with Tf2O (2.221 ml, 13.15 mmol). After 15 min, the reaction mixture was poured into sat. aq. NaHCO3 and extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was dissolved in 1,4-Dioxane (21.74 ml)/Water (4.35 ml), treated with 4-methylphenyl boronic acid (1.251 g, 9.20 mmol) and Na2CO3 (2.091 g, 19.72 mmol) and then degassed with N2 for 5 min. Pd(PPh3)4 (0.759 g, 0.657 mmol) was added and the reaction mixture was warmed to 80° C. After 2 h, the reaction mixture was poured into sat. aq. NH4Cl and extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. the residue was loaded onto celite and purified by ISCO (0-50% EtOAc-hexanes) to afford methyl 5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridine-8-carboxylate (400 mg, 0.869 mmol, 13.21% yield) as a yellow foam. 1H NMR (400 MHz, CHLOROFORM-d)=7.17 (d, 6H), 7.03-6.96 (m, 2H), 5.83 (s, 2H), 3.96 (s, 2H), 3.86 (t, J=5.6 Hz, 2H), 3.60 (s, 3H), 3.56 (s, 3H), 2.64 (t, J=5.5 Hz, 2H), 2.40 (s, 3H).

Provenance & Evidence