4-Bromoaniline → HCID 90010431, compound

Participants

Reaction Conditions

Reaction Steps

Step-1: tert-Butyl (4-(2-ethyl-5-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyridin-3-yl)phenyl)carbamate: To a solution of Intermediate-1a (2.30 g, 8.10 mmol, 1.0 eq) and tert-butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (2.58 g, 8.10 mmol, 1.0 eq; prepared from 4-bromoaniline by following the procedure described in organic and biomolecular chemistry, 2010, 8 (15), 3457) in dioxane (25 mL) was added Pd(PPh3)2Cl2 (284 mg, 0.40 mmol). The resulting mixture was thoroughly deoxygenated by subjecting to vacuum/nitrogen cycle three times and the reaction mixture was heated to 75° C. and further maintained for 15 h under nitrogen atmosphere. The resulting mixture was cooled to RT and filtered through celite. The filtrate was concentrated under vacuum and the crude product was purified by flash column chromatography (silica gel, ethyl acetate-hexanes system as eluent) to afford 2.80 g (78%) of the desired compound as a white solid. 1HNMR (400 MHz, CDCl3) δ 8.96 (s, 1H), 7.89 (s, 1H), 7.48 (d, J=8.0 Hz, 2H), 7.26 (d, J=8.0 Hz, 2H), 6.75 (s, 1H), 3.51 (s, 3H), 2.84 (q, J=7.0 Hz, 2H), 1.58 (s, 9H), 1.23 (t, J=7.0 Hz, 3H); ESI-MS (m/z) 397 (MH)+

Provenance & Evidence