Potassium Carbonate → 4-Chloro-5,7-difluoro-3-methyl-2-(4-pyridinyl)quinoline

HRID 1431405Notes

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.[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>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:20]=[CH:21][N:16]=[CH:17][CH:18]=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 (1.0 g, 4.03 mmol) in toluene (8.06 mL) was added pyridin-4-ylboronic acid (0.743 g, 6.05 mmol), potassium carbonate (1.11 g, 8.06 mmol) and palladium tetrakistriphenylphosphine (0.466 g, 0.403 mmol). The reaction was stirred at 100° C. and stirring continued for 15 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-(4-pyridinyl)quinoline as a white solid. Mass Spectrum (ESI) m/e=291.1 (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-775584e9ef8a45118125af1b3dd6f91d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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