Potassium Carbonate → HCID 66632601, compound

HRID 1431409Notes

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][O:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:23]=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:22]2[CH:21]=[N:20][CH:19]=[C:18]([O:17][CH3:16])[CH:23]=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 (0.35 g, 1.411 mmol) in toluene (2.80 mL) was added 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.50 g, 2.12 mmol), potassium carbonate (0.585 g, 4.23 mmol) and palladium tetrakistriphenylphosphine (0.163 g, 0.141 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-2-(5-methoxy-3-pyridinyl)-3-methylquinoline as a white solid. Mass Spectrum (ESI) m/e=321.1 (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-4d099c3715af4341862d4dcc210bb0f0
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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