4-Methyl-2-(tributylstannyl)pyridine → 4-Chloro-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline

HRID 1618686Notes

Reaction equation

HRID 1618686 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][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([Sn](CCCC)(CCCC)CCCC)[CH:18]=1>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.C1(C)C=CC=CC=1>[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:18]=[C:17]([CH3:16])[CH:22]=[CH:21][N:20]=2)[C:11]=1[CH3:12]

Participants

5

Reactant 2

HCID 112227754-Methyl-2-(tributylstannyl)pyridineHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 596311504-Chloro-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to procedure E by stirring 2,4-dichloro-5,7-difluoro-3-methylquinoline (1.25 g, 5.04 mmol), 4-methyl-2-(tributylstannyl)pyridine (2.12 g, 5.54 mmol), Pd(PPh3)4 (0.58 g, 0.50 mmol), and toluene (25 mL) at 100° C. for 18 h. Purification by column chromatography (silica gel, 0-20% EtOAc in hexanes) gave 4-chloro-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=305.0 (M+1).

Workup

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

Sources & evidence

ORD record
ord-e2149be211c34e76b915c7e797487667
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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