Sodium hydride → HCID 59170339, compound

HRID 1445898Notes

Reaction equation

HRID 1445898 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+].[CH2:21]([O:23][C:24](=[O:30])[CH:25](Br)[CH:26]([CH3:28])[CH3:27])[CH3:22]>CN(C)C=O.C(OCC)(=O)C>[CH2:21]([O:23][C:24](=[O:30])[CH:25]([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)[CH:26]([CH3:28])[CH3:27])[CH3:22]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79068Ethyl 2-bromoisovalerate2×HCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 1

HCID 59170339HCID 59170339, compoundYield 19.5%

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 ethyl-2-bromoisovalerate (0.344 mL, 1.65 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 (10:1 Hexane:EtOAc) to afford a 1:1 mixture of 7: ethyl-2-bromoisovalerate. Further purification by column chromatography (10:1 Hexane:EtOAc) afforded 7 (0.09 g, 19%) as a yellow oil.

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 (10:1 Hexane:EtOAc)
  7. customto afford
  8. additiona 1:1 mixture of 7
  9. customFurther purification by column chromatography (10:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-d1b980aff94e44e6886df00ea8b24b12
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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