Acetonitrile → 4-Chloro-5,7-difluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

HRID 1618704Notes

Reaction equation

HRID 1618704 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.[CH3:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>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.O>[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]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17][CH3:16])[C:11]=1[CH3:12]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 596313634-Chloro-5,7-difluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Prepared according to procedure F by stirring 2,4-dichloro-5,7-difluoro-3-methylquinoline (550 mg, 2.22 mmol), 2-(methylthio)phenylboronic acid (484 mg, 2.88 mmol), sodium carbonate (705 mg, 6.65 mmol), Pd(PPh3)4 (128 mg, 0.11 mmol), acetonitrile (5.2 mL), and water (1.3 mL) at 100° C. in a microwave reactor for 1 h. Purification by column chromatography (silica gel, 0-20% EtOAc in hexanes) gave 4-chloro-5,7-difluoro-3-methyl-2-(2-(methylthio)phenyl)quinoline as a white amorphous solid. Mass Spectrum (ESI) m/e=336.1 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica gel, 0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2fd2c42c845b47d59124377df1683b8e
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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