Diethyl Ether → 1-[1-(3-Fluorophenyl)-3-methyl-1H-indol-2-yl]ethanone

HRID 2175345Notes

Reaction equation

HRID 2175345 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[C:18](N(OC)C)=[O:19])[CH:5]=[CH:6][CH:7]=1.[CH3:24][Mg]Br.CCOCC>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[C:18](=[O:19])[CH3:24])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 585653381-(3-Fluorophenyl)-N-methoxy-N,3-dimethyl-1H-indole-2-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 585653661-[1-(3-Fluorophenyl)-3-methyl-1H-indol-2-yl]ethanoneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(3-fluorophenyl)-N-methoxy-N,3-dimethyl-1H-indole-2-carboxamide (0.27 g, 0.86 mmol) in tetrahydrofuran (5 mL) was added 3.0 M methylmagnesium bromide in ether (2.3 mL, 6.9 mmol). The reaction was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-15% EtOAc/hexane) to give the desired product (0.165 g, 71%). LCMS calculated for C17H15FNO(M+H)+: m/z=268.1. Found: 268.0.

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica gel (eluting with 0-15% EtOAc/hexane)

Sources & evidence

ORD record
ord-8eeeba7412334b53812c18052e6d8137
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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