Potassium Carbonate → HCID 59132380, compound

HRID 84039Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[CH:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]2[CH:15]=[CH:16][C:11]([CH:9]=[O:10])=[CH:12][CH:13]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-bromo-5-methylpyridine (2 g), (4-formylphenyl)boronic acid (3.5 g), tetrakis(triphenylphosphine)palladium(0) (0.672 g), and potassium carbonate (4.8 g) was dried under high vacuum for 10 minutes and dry dimethylformamide (15 mL) was added at room temperature. The reaction mixture was heated at 110° C. for 6 hours, and then quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to obtain a residue which was purified by column chromatography over silica gel using 20% ethyl acetate in hexane as eluant to afford the title compound (2.8 g).

Workup

customwas dried under high vacuum for 10 minutes
additiondry dimethylformamide (15 mL) was added at room temperature
customquenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with water and brine solution
dry with materialdried over anhydrous sodium sulphate
customThe solvent was evaporated under reduced pressure
customto obtain a residue which
customwas purified by column chromatography over silica gel using 20% ethyl acetate in hexane as eluant

Sources & evidence

ORD record: ord-5b5fdeef4ce84bc58554ed37646c55ef
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846910B2

Reaction notes

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