HCID 86656167, compound → HCID 67248070, compound

HRID 1192479Notes

Reaction equation

HRID 1192479 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18](N(OC)C)=[O:19])=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2.[CH3:24][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18](=[O:19])[CH3:24])=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2

Participants

4

Reactant 2

HCID 86656167HCID 86656167, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67248070HCID 67248070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide (63 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 C17H13FNO(M+H)+: m/z=266.1; found: 266.0.

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-42f6267334a54ce9a5010e18f49b5f7d
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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