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

HRID 1264509Notes

Reaction equation

HRID 1264509 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>[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

6

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 1

HCID 6228DimethylformamideSolvent2×

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, 148-149° 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. Caled for C18H20N2O1: C, 77.11; H, 7.19; N, 9.98. Found: C, 76.44; H, 7.21; N, 9.96.

Workup

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

Sources & evidence

ORD record
ord-ccb320d96d8e4569a27f6ab8cc69699f
Source dataset
uspto-grants-2003_04
Patent number
US06544970B2

Reaction notes

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