Benzocaine → HCID 59618079, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL microwave tube containing N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.50 g, 1.40 mmol), ethyl 4-aminobenzoate (0.31 g, 1.92 mmol), Pd2(dba)3 (40 mg, 0.043 mmol), Cs2CO3 (0.94 g, 2.91 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 17 mg, 0.029 mmol), and dioxane (20 mL) was degassed and then charged by N2 (3×). The mixture was then heated at 120° C. for 30 min and then diluted with dioxane (20 mL). The reaction was filtered through Celite and concentrated under reduced pressure. The residue was purified by reverse-phase HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80%, 10 min) to afford ethyl 4-(4-(2,6-dichlorobenzamido)pyridin-2-ylamino)benzoate (500 mg, yield: 80%). 1H NMR (400 MHz, DMSO) δ 11.02 (s, 1H), 9.60 (s, 1H), 8.15 (d, J=5.6, 1H), 7.96-7.76 (m, 4H), 7.57 (ddd, J=16.0, 9.0, 4.2, 4H), 6.92 (dd, J=5.6, 1.6, 1H), 4.27 (q, J=7.1, 2H), 1.31 (t, J=7.1, 3H). LCMS (ESI) m/z: 431.4 [M+H+].

Provenance & Evidence