Magnesium → HCID 86659889, compound

HRID 2360168Notes

Reaction equation

HRID 2360168 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]([C:7]1[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:16][CH3:17])=[CH:11][CH:10]=2)=[O:6])[CH2:2][CH3:3].[Mg]>CO.C(OCC)(=O)C>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH3:17])[CH:13]=2)[N:8]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:6])[CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 86659890HCID 86659890, compound

Product 1

HCID 86659889HCID 86659889, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(di-n-propylaminocarbonyl)-5-methoxy-1-benzylindole (654 mg, 1.79 mmol) in 18 mL of methanol was added magnesium turnings (0.87 g, 36 mmol) at 0° C. After the reaction mixture was stirred for 12 h with slowly warming up to room temperature, the reaction mixture was diluted with ethyl acetate, and washed with 1 M HCl, saturated NaHCO3 aqueous solution and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography to obtain the title compound (405 mg, 62%).

Workup

  1. washwashed with 1 M HCl, saturated NaHCO3 aqueous solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-401b87db6e5444288121d545c0b92e31
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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