Tetrahydrofuran → 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butylcarbamoyl)benzoic acid

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Sodium hydride (0.827 g, 20.67 mmol) was suspended in THF (10 mL), and then 2-(3,4-dihydroxybutyl)isoindoline-1,3-dione (3.24 g, 13.78 mmol) in THF (20.0 mL) was added. This reaction mixture was stirred at 0° C. for 10 min, followed by the addition of 1-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (2.041 g, 9.19 mmol) in THF (16.0 mL). The mixture was stirred at 0° C. for 1 h and then stirred for an additional 2 h at rt. The reaction was quenched with water and washed with EtOAc. The aqueous layer was acidified to pH 2˜4 and then extracted with EtOAc. The combined EtOAc layers were concentrated in vacuo to get 2-(3-hydroxy-4-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)butylcarbamoyl)benzoic acid, which is used as-is in the next step. LC-MS (M+H)+=456.1. 1H NMR (500 MHz, methanol-d4) δ 9.31 (s, 1H), 8.15-8.01 (m, 3H), 7.86-7.76 (m, 2H), 7.51-7.46 (m, 2H), 4.43-4.42 (m, 1H), 4.29-4.27 (m, 1H), 3.91-3.87 (m, 1H), 3.63-3.47 (m, 2H), 2.47 (s, 3H), 2.05-1.98 (m, 1H), 1.87-1.84 (m, 1H).

Herkunft & Nachweise