Methyl iodide → 3-Bromo-2-methylthieno[2,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of 3-bromothieno[2,3-c]pyridine (250 mg, 1.17 mmol) in THF (10 mL) was added 1.5 M lithium diisopropylamide in cyclohexane (0.86 mL, 1.28 mmol) and the mixture stirred at −78° C. for 15 min. Methyl iodide (80 μL, 1.28 mmol) was added at −78° C. The mixture was stirred from −78° C. to room temperature and stayed at room temperature for 30 min. Saturated aqueous NH4Cl solution was added and the mixture extracted with DCM. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The crude product was purified by ISCO chromatography (0 to 25% EtOAc:heptane) to afford 178 mg (67%) of the title compound as a white solid. 1H NMR (400 MHz, CD3Cl): δ 8.81 (s, 1 H), 8.39 (d, J=5.6 Hz, 1 H), 7.36 (dd, J=5.3, 0.8 Hz, 1 H), 2.41 (s, 3 H); MS (ESI): 228.30, 230.30 [M+H]+; HPLC tR=0.68 min (HPLC: Analytical—2 min).

Provenance & Evidence