HCID 58368653, compound → HCID 58368424, compound

HRID 1192566Notes

Reaction equation

HRID 1192566 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:20](N(OC)C)=[O:21])=[CH:10][C:11]([CH:18]=[CH2:19])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.[CH3:26][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:20](=[O:21])[CH3:26])=[CH:10][C:11]([CH:18]=[CH2:19])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 58368653HCID 58368653, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58368424HCID 58368424, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 8-(3-fluorophenyl)-N-methoxy-N-methyl-5-vinylquinoline-7-carboxamide (32 mg, 0.095 mmol) in tetrahydrofuran (0.2 mL) was added 1.4 M methylmagnesium bromide in tetrahydrofuran (0.20 mL, 0.29 mmol) at 0° C. The reaction was stirred at room temperature for 1 hour, quenched with sat. ammonium chloride. The resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated to dryness. The crude product was used directly in the next step (26 mg, 94%). LCMS calculated for C19H15FNO (M+H)+: m/z=292.1; Found: 292.1.

Workup

  1. customquenched with sat. ammonium chloride
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d7d4e81a5a8445e0a5747f727cef9fca
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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