تفاعل #7096

معادلة التفاعل

water

5′-(1H-pyrrole-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one

potassium carbonate

iodomethane

→

subtitled compound

المردود 92.3%

5′-(1-Methyl-pyrrole-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one

المردود 92.3%

المذيبات

DMF

EtOAc

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe layers were separated
2. 2
   استخلاصthe aqueous layer was extracted with EtOAc (2×100 mL)
3. 3
   غسيلwashed with brine (15 mL)
4. 4
   تجفيفdried over MgSO4
5. 5
   ترشيحThe solution was filtered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىthe residue was purified by flash column chromatography on silica gel (eluting with 40% EtOAc/hexane)

الإجراء التجريبي

A mixture of 5′-(1H-pyrrole-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (0.46 g, 1.7 mmol) and potassium carbonate (5 eq, 1.18 g, 8.6 mmol) in DMF (2 mL) at room temperature was treated with a solution of iodomethane (3 eq, 0.32 g, 5.1 mmol) in DMF (1 mL). The solution was stirred 16 h at room temperature, then poured into water (10 mL). EtOAc (15 mL) was added, the layers were separated, and the aqueous layer was extracted with EtOAc (2×100 mL). The organic layers were combined, washed with brine (15 mL) and dried over MgSO4. The solution was filtered, concentrated in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with 40% EtOAc/hexane) to give the subtitled compound (0.44 g, 76%) as a white powder, mp 148–9° C. 1H NMR (DMSO-d6; 400 MHz) δ 1.50–1.62 (m, 3H), 1.62–1.82 (m, 5H), 1.83–1.94 (m, 2H), 3.11 (s, 3H), 6.08 (m, 1H), 6.42 (m, 1H), 6.79 (m, 1H), 6.97 (d, 1H, J=8.1 Hz), 7.51 (dd, 1H, J=8.1, 1.8 Hz), 7.70 (d, 1H, J=1.7 Hz), 11.20 (br s, 1H). Anal. Calcd for C18H20N2O1: C, 77.11; H, 7.19; N, 9.98. Found: C, 76.44; H, 7.21; N, 9.96.

المصدر