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Sodium Carbonate → HCID 66990340, compound

HRID 454670
Notes
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Reaction equation

HRID 454670 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:17]([O:24][C:25]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)=[CH:44][C:26]=1[C:27]([NH:29][C:30]1[CH:42]=[C:41](Br)[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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.COCCOC>[CH2:17]([O:24][C:25]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)=[CH:44][C:26]=1[C:27]([NH:29][C:30]1[CH:42]=[C:41]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 66990213HCID 66990213, compound

Product 1

HCID 66990340HCID 66990340, compoundYield 98.1%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalyst
HCID 962
Water
Solvent
2×
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Water (0.60 mL), 2-methylphenylboronic acid (0.029 g), sodium carbonate (0.047 g), and bis(triphenylphosphine)palladium(II) dichloride (2.5 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-bromobenzoate (0.10 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: 99-91% hexane/ethyl acetate] to obtain 0.10 g of tert-butyl 2-(2-(benzyloxy)-5-(piperidin-1-yl)benzamido)-4-(2-methylphenyl)benzoate.

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: 99-91% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-ba5201f78b1c4608ad22e313f3db7548
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492582B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes