N-methoxy-N,3-dimethylthiophene-2-carboxamide → (4-Ethylphenyl)(3-methylthiophen-2-yl)methanone

HRID 1469203Notes

Reaction equation

HRID 1469203 reaction equation
CON(C)[C:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH3:11])=[O:5].[CH2:13]([C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1)[CH3:14]>C1COCC1>[CH2:13]([C:15]1[CH:20]=[CH:19][C:18]([C:4]([C:6]2[S:7][CH:8]=[CH:9][C:10]=2[CH3:11])=[O:5])=[CH:17][CH:16]=1)[CH3:14]

Participants

4

Reactant 2

HCID 10511733N-methoxy-N,3-dimethylthiophene-2-carboxamideHCID 178436501HCID 178436501, compound

Product 1

HCID 43462876(4-Ethylphenyl)(3-methylthiophen-2-yl)methanoneYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N,3-dimethylthiophene-2-carboxamide (52) (J. Med. Chem., 2001, 44, 863) (5.00 g, 27.0 mmole) in THF (30 mL) was added 4-ethylphenylmagnesium bromide (0.5M in THF, 108 mL, 54.0 mmole) at 0° C. The resulting solution was stirred at ambient temperature overnight. The reaction mixture was quenched by adding MeOH (20 mL) and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the compound 53 (4-ethylphenyl)(3-methylthiophen-2-yl)methanone (4.42 g, 19.2 mmole, 71%) as brown oil.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding MeOH (20 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record
ord-41274e00e75241588de44a9049ac9606
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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