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

HRID 1431417Notes

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:18]=[CH:19][C:20]([Sn](CCCC)(CCCC)CCCC)=[N:21][CH:22]=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:20]2[CH:19]=[CH:18][C:17]([CH3:16])=[CH:22][N:21]=2)[C:11]=1[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 2,4-dichloro-5,7-difluoro-3-methylquinoline (0.6 g, 2.419 mmol) in toluene (4.84 mL) was added 5-methyl-2-(tributylstannyl)pyridine (1.02 g, 2.66 mmol), and palladium tetrakistriphenylphosphine (0.280 g, 0.24 mmol). The reaction was stirred at 100° C. and stirring continued for 42 h. The reaction mixture was cooled to rt and concentrated in vacuo. The crude material was purified by column chromatography on silica gel, eluting with 0-50% EtOAc in hexanes to provide 4-chloro-5,7-difluoro-3-methyl-2-(5-methyl-2-pyridinyl)-quinoline as a white solid. Mass Spectrum (ESI) m/e=305.0 (M+1).

Workup

stirringstirring
temperatureThe reaction mixture was cooled to rt
concentrationconcentrated in vacuo
customThe crude material was purified by column chromatography on silica gel
washeluting with 0-50% EtOAc in hexanes

Sources & evidence

ORD record: ord-dc68589590c44711911efd5ed225fe9a
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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