3-Methyl-2-(tributylstannyl)pyridine → HCID 59631185, compound

HRID 1431401Notes

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[C:18]([Sn](CCCC)(CCCC)CCCC)=[N:19][CH:20]=[CH: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:18]2[C:17]([CH3:16])=[CH:22][CH:21]=[CH:20][N:19]=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 (0.17 g, 0.685 mmol) in toluene (1.40 mL) was added 3-methyl-2-(tributylstannyl)pyridine (0.29 g, 0.75 mmol), and palladium tetrakistriphenylphosphine (0.079 g, 0.069 mmol). The reaction was stirred at 100° C. and stirring continued for 68 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-(3-methylpyridin-2-yl)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-118495e4aa124836832a2cca45f64183
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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