反応 #476719

反応方程式

Methyl iodide

lithium diisopropylamide

cyclohexane

3-bromothieno[2,3-c]pyridine

NH4Cl

→

title compound

収率 67.0%

3-bromo-2-methylthieno[2,3-c]pyridine

収率 67.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred from −78° C. to room temperature
2. 2
   workup.WAITstayed at room temperature for 30 min
3. 3
   抽出the mixture extracted with DCM
4. 4
   洗浄The organic layer was washed with brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他The crude product was purified by ISCO chromatography (0 to 25% EtOAc:heptane)

実験手順

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).

出典