Sodium hydride → Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate

Participants

Reaction Conditions

Reaction Steps

3-Azido-1-propanol (0.266 mL, 3.64 mmol) was dissolved in DMF (5 mL) and cooled to 0° C. NaH (146 mg, 3.64 mmol) was added and the mixture was stirred for 15 minutes. Diethyl-4-bromo-2,6-pyridinedicarboxylate was dissolved in DMF (5 mL) an added to the reaction mixture dropwise. The reaction was complete as indicated by TLC in 1 hour. The reaction mixture was partitioned between CH2Cl2 and water. The water was separated and extracted with CH2Cl2. The CH2Cl2 layers were combined, dried (MgSO4) and concentrated to an oil. The oil was purified by silica gel flash column chromatography to give a yield of 40%. 1H NMR (CDCl3) δ 1.44 (t, 6H, 2× CH2), 2.11 (m, 2H, CH2), 3.54 (t, 2H, CH2), 4.23 (t, 2H, CH2), 4.45 (q, 4H, 2× CH2), 7.78 (2, 2H, 2× Ar).

Provenance & Evidence