Sodium Carbonate → HCID 86657029, compound

HRID 1909121Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:15]2[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=2[F:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 2,6-dichloroisonicotinate (3.34 g, 16.2 mmol) in toluene (100 mL) were added (2-fluoro-4-methylphenyl)boronic acid (1.4 g, 9.09 mmol), (tetrakistriphenylphosphine)palladium (0) (0.94 g, 0.81 mmol) and sodium carbonate (2.0 M in water; 8.1 g, 16.2 mmol). The mixture was degassed with nitrogen (3×) and heated to 80° C. After 42 h, the mixture was cooled to ambient temperature and saturated NaHCO3 was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 85% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (1.07 g). MS 280.0 (M+1).

Workup

customThe mixture was degassed with nitrogen (3×)
temperaturethe mixture was cooled to ambient temperature
additionsaturated NaHCO3 was added
extractionThe mixture was extracted with ethyl acetate (3×)
washThe combined organic extracts were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by reverse phase chromatography (C-18, 85% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-51903cb5ede74d548dcbd5199750be43
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598209B2

Reaction notes

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