Diethyl Ether → HCID 58565344, compound

HRID 2175333Notes

Reaction equation

HRID 2175333 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)[CH:10]=[C:9]2[C:17](N(OC)C)=[O:18])[CH:5]=[CH:6][CH:7]=1.[CH3:23][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)[CH:10]=[C:9]2[C:17](=[O:18])[CH3:23])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58565348HCID 58565348, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58565344HCID 58565344, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(3-fluorophenyl)-N-methoxy-N-methyl-1H-indole-2-carboxamide (0.52 g, 1.7 mmol) in tetrahydrofuran (10 mL) was added 3.0 M methylmagnesium bromide in ether (4.6 mL, 0.014 mol). 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 washed with water and brine, dried over MgSO4, and concentrated to give crude product (0.4 g, 91%). The crude product was used directly in next step. LCMS calculated for C16H13FNO(M+H)+: m/z=254.1. Found: 254.1.

Workup

  1. customThe reaction was quenched with saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a74de1db0c23470d9b1311520148f29d
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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