Toluene → Methyl 4-pyridin-3-ylbenzoate

HRID 1274255Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1.18 g 4-iodobenzoic acid methyl ester, 830 mg pyridine-3-boronic acid, and 158 mg bis(triphenylphosphine) palladium(II) chloride was added solvent (18 mL toluene and 5 mL methanol) followed by 4.5 mL of 2M sodium carbonate and the mixture heated to 80° C. on an oil bath. After 16 hours the mixture was cooled to room temperature diluted with ethyl acetate and filtered through diatomaceous earth. The organic portion was washed sequentially with 1.25N sodium hydroxide and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 80:20; then 70:30; then 60:40) gave the title compound (810 mg).

Workup

temperatureAfter 16 hours the mixture was cooled to room temperature
filtrationfiltered through diatomaceous earth
washThe organic portion was washed sequentially with 1.25N sodium hydroxide and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customPurification by flash chromatography on silica gel (hexane

Sources & evidence

ORD record: ord-b642de944d394bc2858e23985720466e
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156772

Reaction notes

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