2,4-Dichloro-5,7-difluoro-3-methylquinoline → 4-Chloro-5,7-difluoro-3-methyl-2-(3-(trifluoromethyl)benzyl)quinoline

HRID 1618684Notes

Reaction equation

HRID 1618684 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.[Cl-].[F:17][C:18]([F:28])([F:27])[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][Zn+]>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>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([C:18]([F:17])([F:27])[F:28])[CH:20]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinolineHCID 178506157HCID 178506157, compound

Product 1

HCID 866642794-Chloro-5,7-difluoro-3-methyl-2-(3-(trifluoromethyl)benzyl)quinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to procedure Z using 2,4-dichloro-5,7-difluoro-3-methylquinoline (350 mg, 1.411 mmol), Pd(PPh3)4 (163 mg, 0.14 mmol), 3-(trifluoromethyl)benzylzinc chloride (0.5M in THF, 2.96 mL, 1.48 mmol), and THF (3.5 mL). Purification by column chromatography (silica gel, 0-8% EtOAc in hexanes) gave 4-chloro-5,7-difluoro-3-methyl-2-(3-(trifluoromethyl)benzyl)-quinoline as a white solid. Mass Spectrum (ESI) m/e=372.0 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica gel, 0-8% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3b228e653d85471085fb12a1885d6eb1
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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