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

HRID 1245169Notes

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[CH:8]=[CH:9][C:10](OS(C(F)(F)F)(=O)=O)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].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[CH:8]=[CH:9][C:10]([C:52]2[CH:53]=[CH:54][N:55]=[CH:56][CH:57]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (1.43 g, 2.8149 mmol) in toluene (32 ml) were added tetrakistriphenylphosphine palladium (98 mg, 0.0848 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 3.66 ml), lithium chloride (239 mg, 5.6381 mmol) and ethanolic solution (5.9 ml) of pyridine-4-boronic acid pinacol cyclic ester (866 mg, 4.2243 mmol) and the mixture was heated with stirring at 95° C. for 16 hours. The reaction solution was diluted with ethyl acetate (200 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 (910 mg, 2.0823 mmol, 74%).

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-9a2e228ebf494ae59aabfa46a4094819
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122543B2

Reaction notes

Loading…