Sodium hydride → HCID 59170342, compound

HRID 1445914Notes

Reaction equation

HRID 1445914 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:28])[CH:25]([F:27])Br)[CH3:22]>CN(C)C=O.C(OCC)(=O)C>[CH2:21]([O:23][C:24](=[O:28])[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)[F:27])[CH3:22]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl esterHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 1

HCID 59170342HCID 59170342, compoundYield 32.5%

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 (50 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-bromofluoroacetate (0.2 mL, 1.65 mmole) was added. The mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (500 mL) and washed with H2O (5×100 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 6 (0.14 g, 32%) as an yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. washwashed with H2O (5×100 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-d59406349a8b492f83b3e87f62813c2c
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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