Sodium hydride → HCID 59170316, compound

HRID 1445901Notes

Reaction equation

HRID 1445901 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21][O:22][C:23](=[O:32])[CH:24](Br)[CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28]>CN(C)C=O.C(OCC)(=O)C>[CH3:30][O:29][C:27](=[O:28])[CH2:26][CH2:25][CH:24]([O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:9]([CH3:18])[N:8]2[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:23]([O:22][CH3:21])=[O:32]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1365751,5-Dimethyl 2-bromopentanedioateHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 1

HCID 59170316HCID 59170316, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-2-methyl-1H-indol-4-ol 3 (0.3 g 1.26 mmole) was dissolved in anhydrous dimethylformamide (20 mL). To the solution sodium hydride 60% in mineral oil (66 mg 1.65 mmole) was added. The mixture was stirred at room temperature for 1 h. To the mixture dimethyl-2-bromoglutarate (0.3 mL, 1.25 mmole) was added. The mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (300 mL) and washed with H2O (4×100 mL) and brine (1×100 mL). The organic layer was separated, dried with magnesium sulfate and concentrated. The residue was purified by column chromatography (6:1 Hexane:EtOAc) to afford 9 (0.49 g, 97%) as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. washwashed with H2O (4×100 mL) and brine (1×100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (6:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-e115c10db41f440c97fde3e0f5fd84ff
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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