Sodium Carbonate → Methyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoate

HRID 1245174Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][C:7]1[C:8](OS(C(F)(F)F)(=O)=O)=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].B1([C:52]2[CH:57]=[CH:56][N:55]=[CH:54][CH:53]=2)OC(C)(C)C(C)(C)O1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][C:7]1[C:8]([C:52]2[CH:57]=[CH:56][N:55]=[CH:54][CH:53]=2)=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of methyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (385 mg, 0.7578 mmol) in toluene (8.6 ml) were added tetrakistriphenylphosphine palladium (26 mg, 0.0224 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 0.99 ml), lithium chloride (64 mg, 1.5097 mmol) and ethanolic solution (1.59 ml) of pyridine-4-boronic acid pinacol cyclic ester (233 mg, 1.1365 mmol) and the mixture was heated with stirring at 95° C. for 16 hours. The reaction solution was diluted with ethyl acetate (100 ml), washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (301 mg, 0.6887 mmol, 91%).

Workup

temperaturethe mixture was heated
washwashed with water
customdried
customthe solvent was evaporated
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-10a2472ca1494c3ca5a2aff46193bf8b
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122543B2

Reaction notes

Loading…