Potassium Carbonate → HCID 89648349, compound

Participants

Reaction Steps

Following procedure A, 4-(2-methylpentan-2-yl)phenol (52 mg, 0.29 mmol, 1.00 eq) and 2-chloro-5-nitropyridine (57 mg, 0.36 mmol, 1.23 eq) were dissolved in DMSO (6 mL). Anhydrous K2CO3 (66 mg, 0.48 mmol, 1.65 eq) was added and the reaction mixture was stirred at room temperature for 27 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:50) to afford the title compound as colourless solid (86 mg, 0.29 mmol, 98% yield). Rf=0.50 (EtOAc/PE 1:10). HRMS (ESI) calcd. for C17H21N2O3+ [M+H]+ 301.1547. found: 301.1545. 1H NMR (400 MHz, CDCl3) δ 9.07 (d, J=2.7 Hz, 1H, aromatic H), 8.46 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.45-7.35 (m, 2H, aromatic H), 7.14-7.05 (m, 2H, aromatic H), 6.99 (dd, J=9.0, 0.6 Hz, 1H, aromatic H), 1.65-1.54 (m, 2H, C(CH3)2CH2CH2CH3), 1.32 (s, 6H, C(CH3)2CH2CH2CH3), 1.19-1.05 (m, 2H, C(CH3)2CH2CH2CH3), 0.84 (t, J=7.3 Hz, 3H, C(CH3)2CH2CH2CH3). 13C NMR (101 MHz, CDCl3) δ 167.17, 150.43, 147.69, 145.21, 140.26, 134.90, 127.44, 120.72, 111.29, 47.27, 37.74, 29.07, 18.08, 14.87.

Provenance & Evidence