Reaktion #7096

Reaktionsgleichung

water

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

potassium carbonate

iodomethane

→

subtitled compound

Ausbeute 92.3%

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

Ausbeute 92.3%

Lösungsmittel

DMF

EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers were separated
2. 2
   Extraktionthe aqueous layer was extracted with EtOAc (2×100 mL)
3. 3
   Waschenwashed with brine (15 mL)
4. 4
   Trocknendried over MgSO4
5. 5
   FiltrationThe solution was filtered
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigethe residue was purified by flash column chromatography on silica gel (eluting with 40% EtOAc/hexane)

Vorschrift

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.

Quelle