Water → HCID 10051762, compound

HRID 1058972Notes

Reaction equation

HRID 1058972 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])[CH2:25][CH2:24]2)=[O:22])=[CH:16][C:15]([CH3:37])=[CH:14][CH:13]=3)=[CH:6][CH:5]=1.I[CH3:39].O>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([CH3:39])[C:12]3[C:17]([C:18]=2[CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])[CH2:25][CH2:24]2)=[O:22])=[CH:16][C:15]([CH3:37])=[CH:14][CH:13]=3)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18669082HCID 18669082, compound

Product 1

HCID 10051762HCID 10051762, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 2.5 mg, 0.062 mmol) was added to a solution of 1-{3-[2-(4-chlorophenyl)-5-methyl-1H-indol-3-yl]-1-oxopropyl}-4-(2-methoxyphenyl)piperazine (Example 119, 20 mg, 0.041 mmol) in N,N-dimethylformamide (1 mL) and the mixture was stirred at room temperature for 10 min. Iodomethane (5 μl, 0.12 mmol) was added and the mixture was stirred at room temperature for 10 min. Water (25 mL) was added and the mixture was extracted with ethyl acetate. The combined organic fractions were dried (MgSO4), the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with hexane/ether (35:65) to give the title compound as a pale yellow foam (20 mg, 97%). 1H NMR (360 MHz, CDCl3) δ7.48-7.43 (3H, m), 7.33-7.31 (2H, m), 7.24-7.21 (1H, m), 7.11-7.02 (2H, m), 6.91-6.84 (3H, m), 3.86 (3H, s), 3.76 (2H, m), 3.53 (3H, s), 3.38 (2H, m), 3.04 (2H, m), 2.94 (2H, m), 2.77 (2H, m), 2.57 (2H, m), and 2.49 (3H, s). m/z (ES+) 502, 504 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography on silica gel
  6. washeluting with hexane/ether (35:65)

Sources & evidence

ORD record
ord-6c16e70aebe64d72bc0a3e3751fb621c
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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