N-Methylethylamine → HCID 70654750, compound

Participants

Reaction Steps

To a 0° C. solution of 4-bromo-2-methylbenzenesulfonyl chloride (1.00 g, 3.71 mmol) in CH2Cl2 (10 mL) was added N-ethyldiisopropylamine (0.71 mL, 4.31 mmol) and N-methylethylamine (0.96 mL, 11.13 mmol). The cold bath was removed and the reaction was stirred for 2 h. At completion, the reaction was concentrated, and the crude material was dissolved in CH2Cl2 (20 mL). The mixture was washed with 0.5 N aqueous HCl (3×10 mL), sat. aq. NaHCO3 (2×10 mL), water (10 mL), and saturated aqueous NaCl (5 mL), dried (Na2SO4), and concentrated to give 4-bromo-N-ethyl-2,N-dimethyl-benzenesulfonamide (0.91 g, 3.11 mmol, 85% yield). This material was directly dissolved in 1,4-dioxane (10 mL) and treated with bisboron pinacol ester (0.87 g, 3.43 mmol), PdCl2(dppf)-DCM (69 mg, 0.093 mmol), and KOAc (0.92 g, 9.34 mmol). The reaction was heated at 85° C. for 2 h. At completion, the reaction was cooled to room temperature and concentrated. The crude material was treated with CH2Cl2 (30 mL) and water (10 mL). The organic layer was washed with water (2×10 mL) and brine (5 mL), dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography over silica gel (5-20% EtOAc:hexane eluent) to give N-ethyl-2,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (0.64 g, 60% yield). 1H NMR (300 MHz, MeOH) δ ppm 7.80-7.88 (m, 1H), 7.68-7.77 (m, 2H), 3.26 (q, J=7.12 Hz, 2H), 2.83 (s, 3H), 2.61 (s, 3H), 1.37 (s, 12H), 1.17 (t, J=7.15 Hz, 3H). MS (EI) m/z: 340 [M+H]+. HPLC (Sunfire C18 4.6 mm×50 mm, 10-90% MeCN:10 mM aq NH4OAc, 2 min gradient) tR=2.48 min, 91% integrated area.

Provenance & Evidence