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

HRID 1245168
Notes
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Reaction equation

HRID 1245168 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: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:8]=[CH:9][C:10]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 21919171HCID 21919171, compound

Product 1

HCID 21919126Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoateYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

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-3-boronic acid 1,3-propanediol cyclic ester (684 mg, 4.2222 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 (1.20 g, 2.7459 mmol, 98%).

Workup

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

Sources & evidence

ORD record
ord-6eff5ad309f6484cb8e2dfd761a059cb
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122543B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes