Water → 5'-(1-Methyl-pyrrole-2-yl)spiro[cyclohexane-1,3'-[3h]indol]-2'(1'h)-one

HRID 852495Notes

Reaction equation

HRID 852495 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]12[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[C:21](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C.CCOC(C)=O>[CH3:21][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]12[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 220193735'-(1h-Pyrrol-2-yl)spiro[cyclohexane-1,3'-[3h]indol]-2'(1'h)-one

Product 1

HCID 220193585'-(1-Methyl-pyrrole-2-yl)spiro[cyclohexane-1,3'-[3h]indol]-2'(1'h)-oneYield 92.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5′-(1H-pyrrol-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.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  3. washwashed with brine (15 mL)
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel (eluting with 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-ae3a56aed93d4852b7ddd63e02151334
Source dataset
uspto-grants-2007_08
Patent number
US07253203B2

Reaction notes

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