Methyl iodide → HCID 44242881, compound

HRID 227299Notes

Reaction equation

HRID 227299 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[C:17]3[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:34]I>C1COCC1.O.CCOC(C)=O>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH3:34])[N:18]=[C:17]3[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:24])=[O:25])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178527301HCID 178527301, compound

Product 1

HCID 44242881HCID 44242881, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(4-benzylpiperazin-1-yl)-3-(phenylsulfonyl)-1H-indazole (433 mg, 1.00 mmol) in THF at room temperature is treated with NaH (80 mg, 60% in mineral oil, 2.00 mmol), stirred for 0.5 h, treated with methyl iodide (142 mg, 1.00 mmol), stirred for 16 h, and diluted with water and EtOAc. The organic phase is separated, dried over MgSO4, and concentrated in vacuo. The resultant residue is chromatographed (SiO2, 90:10 EtOAc:hexanes as eluent) to afford the title compound as a white solid, 190 mg (43% yield), mp 195-197° C., identified by mass spectral and NMR analyses.

Workup

  1. stirringstirred for 16 h
  2. customThe organic phase is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is chromatographed (SiO2, 90:10 EtOAc:hexanes as eluent)

Sources & evidence

ORD record
ord-ed231522cff142d892a9444259b4743a
Source dataset
uspto-grants-2009_07
Patent number
US07560470B2

Reaction notes

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