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

HRID 1245166Notes

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:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9](OS(C(F)(F)F)(=O)=O)[CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].B1([C:49]2[CH:54]=[CH:53][CH:52]=[N:51][CH:50]=2)OCCCO1>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:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)[CH:8]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of methyl 4-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (333 mg, 0.6555 mmol) in toluene (6 ml) were added tetrakistriphenylphosphine palladium (23 mg, 0.0199 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 1.00 ml), lithium chloride (56 mg, 1.3241 mmol) and ethanolic solution (1.3 ml) of pyridine-3-boronic acid 1,3-propanediol cyclic ester (159 mg, 0.9814 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 (284 mg, 0.6498 mmol, 99%).

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-7b6c9ea3ae8f47a6a1218c824c09437c
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122543B2

Reaction notes

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