Sodium Bicarbonate → HCID 66990567, compound

HRID 454582Notes

Reaction equation

HRID 454582 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.C(=O)(O)[O-].[Na+].[C:14]([O:17][C:18]1[CH:42]=[CH:41][C:40](Br)=[CH:39][C:19]=1[C:20]([NH:22][C:23]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])=[O:21])(=[O:16])[CH3:15]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.O.COCCOC>[C:14]([O:17][C:18]1[CH:42]=[CH:41][C:40]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:39][C:19]=1[C:20]([NH:22][C:23]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])=[O:21])(=[O:16])[CH3:15]

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734357Furan-2-boronic acidHCID 66990558HCID 66990558, compound

Product 1

HCID 66990567HCID 66990567, compoundYield 53.6%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (0.42 mL), 2-furanboronic acid (0.040 g), sodium bicarbonate (0.060 g), and bis(triphenylphosphine)palladium(II) dichloride (4 mg) were added to an ethylene glycol dimethyl ether (1.4 mL) suspension of methyl 2-(2-acetoxy-5-bromobenzamido)-4-phenylbenzoate (0.14 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour and 10 minutes. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-70% hexane/ethyl acetate] and further purified by silica gel column chromatography [eluent: 90-70% hexane/ethyl acetate] to obtain 0.073 g of methyl 2-(2-acetoxy-5-(furan-2-yl)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour and 10 minutes
  3. customThe insoluble substance was removed by filtration
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-70% hexane/ethyl acetate]
  9. customfurther purified by silica gel column chromatography [eluent: 90-70% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-e6d319715a4b42f19f5dce781848ba83
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…