HCID 58368453, compound → HCID 58368681, compound

HRID 1192540Notes

Reaction equation

HRID 1192540 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH3:18])=[N:10][C:9]=2[C:19](N(OC)C)=[O:20])[CH:5]=[CH:6][CH:7]=1.[CH3:25][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH3:18])=[N:10][C:9]=2[C:19](=[O:20])[CH3:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 58368453HCID 58368453, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58368681HCID 58368681, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-(3-fluorophenyl)-N-methoxy-N,1-dimethylisoquinoline-3-carboxamide (257 mg, 0.792 mmol) in tetrahydrofuran (1 mL) was added 1.4 M methylmagnesium bromide in tetrahydrofuran (3.4 mL, 4.8 mmol). The reaction was stirred at room temperature overnight, quenched with sat. ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to dryness to afford the desired product (0.221 g, 100%). LCMS calculated for C18H15FNO (M+H)+: m/z=280.1; Found: 280.1.

Workup

  1. customquenched with sat. 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

Sources & evidence

ORD record
ord-e47f4355d96a47b6aa8781f5cf3274ba
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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