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Ammonium Chloride → 2-Benzyl-4-chloro-5,7-difluoro-3-methylquinoline

HRID 1618652
Notes
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Reaction equation

HRID 1618652 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[Br-].[CH2:17]([Zn+])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[CH2:17]([C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinolineHCID 178419772HCID 178419772, compound

Product 1

HCID 596314902-Benzyl-4-chloro-5,7-difluoro-3-methylquinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

A screw cap vial was sequentially charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (250 mg, 1.00 mmol), tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.10 mmol), and dry THF (2.52 mL). The mixture was then sparged with N2 prior to the addition of benzylzinc(II) bromide (0.5M in THF, 2.12 mL, 1.06 mmol). The reaction was stirred under N2 at 60° C. for 2 h. The reaction was then cooled to rt, slowly poured over saturated aqueous ammonium chloride and ice, and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and concentrated. The crude product then was triturated with toluene to give 2-benzyl-4-chloro-5,7-difluoro-3-methylquinoline. Mass Spectrum (ESI) m/e=304.0 (M+1).

Workup

  1. customA screw cap
  2. customThe mixture was then sparged with N2
  3. temperatureThe reaction was then cooled to rt
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product then was triturated with toluene

Sources & evidence

ORD record
ord-0969e538fdf246e3b5f8d3037223070e
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765940B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes