1,2-Dimethoxyethane → HCID 66991081, compound

HRID 454710Notes

Reaction equation

HRID 454710 reaction equation
COCCOC.[CH3:7][O:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:24]([O:31][C:32]1[CH:51]=[CH:50][C:49]([CH:52]2[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]2)=[CH:48][C:33]=1[C:34]([NH:36][C:37]1[CH:46]=[C:45](Br)[CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40])=[O:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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>[CH2:24]([O:31][C:32]1[CH:51]=[CH:50][C:49]([CH:52]2[CH2:57][CH2:56][N:55]([CH3:58])[CH2:54][CH2:53]2)=[CH:48][C:33]=1[C:34]([NH:36][C:37]1[CH:46]=[C:45]([C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([O:8][CH3:7])[CH:14]=2)[CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40])=[O:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 66991028HCID 66991028, compound

Product 1

HCID 66991081HCID 66991081, compoundYield 98.4%

Reagents, catalysts & solvents 3

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

Procedure

Ethylene glycol dimethyl ether (0.90 mL), water (0.27 mL), 3-methoxyphenylboronic acid (0.030 g), sodium carbonate (0.044 g), and bis(triphenylphosphine)palladium(II) dichloride (2.3 mg) were added to methyl 2-(2-(benzyloxy)-5-(1-methylpiperidin-4-yl)benzamido)-4-bromobenzoate (0.090 g), followed by heating to reflux under a nitrogen atmosphere for 2 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: 100-92% chloroform/methanol] to obtain 0.093 g of methyl 2-(2-(benzyloxy)-5-(1-methylpiperidin-4-yl)benzamido)-4-(3-methoxyphenyl)benzoate as a light brown solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol]

Sources & evidence

ORD record
ord-62b5dec78d09404b8985cd6a8ad09169
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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