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

HRID 990655Notes

Reaction equation

HRID 990655 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 mnmol) 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 C18H20N2O,: 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-52c2595ad3b2416a8f39a4e01eb47623
Source dataset
uspto-grants-2002_10
Patent number
US06462032B1

Reaction notes

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