Diisopropylethylamine → 5-Cyclopropyl-6-cyclopropylmethoxy-nicotinic acid N'-(4-fluoro-phenyl)-N'-methyl-hydrazide

関与物質

反応手順

In a 10 mL two-necked flask, the above prepared 5-cyclopropyl-6-cyclopropylmethoxy-nicotinic acid (70 mg, 300 μmol, Eq: 1.00) was combined with tetrahydrofuran (3 mL) and DMF (1 mL) to give a colorless solution. TBTU (145 mg, 450 μmol, Eq: 1.5) and N,N-diisopropylethylamine (194 mg, 262 μl, 1.5 mmol, Eq: 5) were added and the reaction mixture stirred for 10 min at rt, before 1-(4-fluorophenyl)-1-methylhydrazine hydrochloride (63.6 mg, 360 μmol, Eq: 1.2, CAN 1978-54-7) was added and the reaction mixture kept overnight at rt. The reaction mixture was quenched with 1 M HCl (10 mL) and extracted with EtOAc (2×20 mL). The organic layers were washed with 1 M NaOH, then with H2O/NaCl solution, combined, dried over Na2SO4 and concentrated in vacuo. The crude material was eventually purified by flash chromatography (silica gel, 20 g, 15% to 40% EtOAc in heptane) to provide 104 mg of the title product as colorless oil; MS (EI) 354.6 (M−H)−.

情報源と証拠