5-chloro-8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide → 1-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanone

HRID 1192489Notes

Reaction equation

HRID 1192489 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](N(OC)C)=[O:13])[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:25][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:13])[CH3:25])[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 866561735-chloro-8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 672495351-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 5-chloro-8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide (40 mg, 0.1 mmol) in tetrahydrofuran (0.2 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (0.50 mL, 0.70 mmol). The reaction was stirred at room temperature overnight, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resultant residue was used directly in next step (32 mg, 92%). LCMS calculated for C17H12ClFNO(M+H)’ : m/z=300.1; found: 284.0.

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a49ff421f2c54796a57f9de4dfbc2c8d
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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