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5-Chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate → 1-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone

HRID 1192508
Notes
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Reaction equation

HRID 1192508 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]=[C:20]([F:24])[CH:19]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.F[C:26](F)(F)S(OC1C(C(N(OC)C)=O)=CC(Cl)=C2C=1N=CC=C2)(=O)=O.C[Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:13])[CH3:26])[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 866561725-Chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonateHCID 866561795-chloro-8-(3-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 672483691-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanoneYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a mixture of 5-chloro-8-(3-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide (154 mg, 0.447 mmol) and 5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (154 mg, 0.386 mmol) in tetrahydrofuran (1 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (3.8 mL, 5.3 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 purified on silica gel, eluting with 0 to 50% of EtOAc in hexane, to give the desired product (38 mg, 32%). LCMS calculated for C17H12ClFNO(M+H)+: m/z=300.1; found: 300.0.

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
  6. customThe resultant residue was purified on silica gel
  7. washeluting with 0 to 50% of EtOAc in hexane

Sources & evidence

ORD record
ord-62f955ff1de541648bead7b0a6ce1939
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680108B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes