HCID 86656164, compound → HCID 67248764, compound

HRID 1192474Notes

Reaction equation

HRID 1192474 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:19](N(OC)C)=[O:20])=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH3:25][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:19](=[O:20])[CH3:25])=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 86656164HCID 86656164, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67248764HCID 67248764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 8-(3,5-difluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide (67 mg, 0.20 mmol) in tetrahydrofuran (0.5 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (0.87 mL, 1.2 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. LCMS calculated for C17H12F2NO(M+H)+: m/z=284.1; 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-ef2814970b0942f3aa4818b56e9f913f
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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