تفاعل #84346

معادلة التفاعل

NH4Cl

4-Toluenesulfonyl chloride

6-fluoro-2,3-dihydro-1H-indole

→

title product

المردود 61.2%

6-fluoro-1-tosylindoline

المردود 61.2%

المذيبات

THF

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىUpon the completion of the reaction
2. 2
   درجة الحرارةthe mixture was cooled to 0° C.
3. 3
   استخلاصextracted with EtOAc (3×10 mL)
4. 4
   غسيلThe combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL)
5. 5
   تجفيفdried (MgSO4)
6. 6
   تركيزThe crude product was concentrated
7. 7
   أخرىdried over high vacuum

الإجراء التجريبي

4-Toluenesulfonyl chloride (460 mg, 2.4 mmol) was slowly added to a solution of 6-fluoro-2,3-dihydro-1H-indole (220 mg, 1.6 mmol) in THF (6 mL) and pyridine (260 μL). The reaction mixture was stirred at room temperature overnight. Upon the completion of the reaction, the mixture was cooled to 0° C., neutralized with aq. sat. NH4Cl (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL) and dried (MgSO4). The crude product was concentrated and dried over high vacuum. Chromatography of the residue (EtOAc/hexanes=1/3) gave 283 mg (0.98 mmol) of the title product. Yield: 61%, colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.67 (d, J=8.2 Hz, 2H), 7.35 (dd, J=10.0, 2.3 Hz, 1H), 7.23 (d, J=8.2 Hz, 2H), 6.97 (m, 1H), 6.62 (m, 1H), 3.90 (t, J=8.4 Hz, 2H), 2.84 (t, J=8.4 Hz, 2H), 2.35 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3): δ 162.5 (d, J=241.4 Hz), 144.5, 143.3 (d, J=11.7 Hz), 133.6, 129.8, 127.2, 127.0 (d, J=2.6 Hz), 125.7 (d, J=9.8 Hz), 110.0 (d, J=22.6 Hz), 102.8 (d, J=28.4 Hz), 50.7, 27.1, 21.5 ppm.

المصدر