Sodium Carbonate → 4-Ethoxycarbonyl-2-(4-fluoro-2-methylphenyl)pyridine

HRID 1436900Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH2:8]([O:7][C:5]([C:4]1[CH:10]=[CH:11][N:12]=[C:2]([C:15]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[CH3:13])[CH:3]=1)=[O:6])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

In a mixed solvent of 250 ml of toluene and 50 ml of ethanol were dissolved 20 g of ethyl 2-chloroisonicotinate and 20 g of 2-methyl-4-fluorophenylboronic acid, and 5.8 g of palladium tetrakistriphenylphosphine and 250 ml of a 2M aqueous sodium carbonate solution, and the mixture was stirred at 50 to 70° C. for 2 hours. The solution was cooled down to room temperature and extracted by adding ethyl acetate and water. The organic layer was further washed with water, and dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1), to give 24.8 g of 4-ethoxycarbonyl-2-(4-fluoro-2-methylphenyl)pyridine as shown in Table 132 below.

Workup

temperatureThe solution was cooled down to room temperature
extractionextracted
additionby adding ethyl acetate and water
washThe organic layer was further washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-1967ab9918e540eba3c5af63e6a7c767
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07619092B2

Reaction notes

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