1,2-Dimethoxyethane → HCID 66990481, compound

HRID 454713Notes

Reaction equation

HRID 454713 reaction equation
COCCOC.CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:28]([O:35][C:36]1[CH:63]=[C:62](I)[CH:61]=[CH:60][C:37]=1[C:38]([NH:40][C:41]1[CH:53]=[C:52]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:51]=[CH:50][C:42]=1[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:39])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>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>[CH2:28]([O:35][C:36]1[CH:63]=[C:62]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[CH:61]=[CH:60][C:37]=1[C:38]([NH:40][C:41]1[CH:53]=[C:52]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:51]=[CH:50][C:42]=1[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:39])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 66990554HCID 66990554, compound

Product 1

HCID 66990481HCID 66990481, compoundYield 49.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalyst3×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Ethylene glycol dimethyl ether (12 mL), water (3.6 mL), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.49 g), sodium carbonate (0.50 g), and bis(triphenylphosphine)palladium(II) dichloride (14 mg) were added to tert-butyl 2-(2-(benzyloxy)-4-iodobenzamido)-4-phenylbenzoate (1.2 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and bis(triphenylphosphine)palladium(II) dichloride (28 mg) was added thereto, followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, and bis(triphenylphosphine)palladium(II) dichloride (28 mg) was added thereto, followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. 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: 80-60% hexane/ethyl acetate] to obtain 0.55 g of tert-butyl 2-(2-(benzyloxy)-4-(pyridin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 4 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. temperatureby heating
  7. temperatureto reflux under a nitrogen atmosphere for 4 hours
  8. temperatureThe reaction mixture was cooled to room temperature
  9. customThe organic layer was separated
  10. washwashed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe obtained residue was purified by silica gel column chromatography [eluent: 80-60% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-05be8d775af541d4827621730b0966c5
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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