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

Temperature

-78 °C

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).

1. stirringThe mixture was stirred from −78° C. to room temperature
2. waitstayed at room temperature for 30 min
3. extractionthe mixture extracted with DCM
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe crude product was purified by ISCO chromatography (0 to 25% EtOAc:heptane)

ORD record

ord-677f4fcaa0644938983a3dd23db72a4b

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378104B2