Water → HCID 71007327, compound

Participants

Reaction Conditions

Reaction Steps

tert-butyl (3-methyl-5-(3-nitropyridin-4-yl)phenyl) carbamate. A glass microwave reaction vessel was charged with tert-butyl (3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (200 mg, 0.60 mmol), 4-chloro-3-nitropyridine (114 mg, 0.72 mmol, Alfa-Aesar), Pd(dppf)Cl2 (25 mg, 0.030 mmol) and 2 M Na2CO3 (aq., 1.20 mL, 2.40 mmol) in dioxane (3 mL). The reaction mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 30 min. Water was then added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anh. Na2SO4, filtered and concentrated. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to provide tert-butyl (3-methyl-5-(3-nitropyridin-4-yl)phenyl)carbamate (198 mg, 0.60 mmol, 100% yield) as a tan solid. MS (ESI, pos. ion) m/z: 330.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 9.06 (s, 1 H), 8.78 (d, J=4.89 Hz, 1 H), 7.42 (d, J=4.89 Hz, 1 H), 7.24-7.27 (m, 1 H), 6.80 (s, 1 H), 6.53 (s, 1 H), 2.37 (s, 3 H), 1.48-1.55 (m, 9 H).

Provenance & Evidence