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Ethyl Acetate → 2-(6-Ethoxy-2-naphthyl)-5-[(2-phenylbutanoyl)amino]benzamide

HRID 503694
Notes
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Reaction equation

HRID 503694 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15](B(O)O)[CH:14]=[CH:13]2)[CH3:8].I[C:24]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:44])[CH:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:36][CH3:37])=[CH:29][C:25]=1[C:26]([NH2:28])=[O:27].C(OCC)(=O)C>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:24]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:44])[CH:35]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:36][CH3:37])=[CH:29][C:25]=1[C:26]([NH2:28])=[O:27])[CH:14]=[CH:13]2)[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 4641693(6-Ethoxynaphthalen-2-yl)boronic acidHCID 594284852-Iodo-5-[(2-phenylbutanoyl)amino]benzamide

Product 1

HCID 116981452-(6-Ethoxy-2-naphthyl)-5-[(2-phenylbutanoyl)amino]benzamide

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1.5 ml of saturated aqueous sodium carbonate solution, 40 mg (0.18 mmol) of 6-ethoxy-2-naphthaleneboronic acid and 14 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium are added to 50 mg (0.12 mmol) of the compound of Example 5A in 3 ml of dioxane. The mixture is stirred at 80° C. overnight and, after addition of 50 ml of ethyl acetate, extracted three times with 50 ml of water. The organic phase is dried over magnesium sulfate and freed of solvent under reduced pressure. The residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 10:90→95:5). 26 mg (44% of theory) of product are obtained.

Workup

  1. extractionextracted three times with 50 ml of water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customThe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 10:90→95:5)
  4. custom26 mg (44% of theory) of product are obtained

Sources & evidence

ORD record
ord-963dd3e2b5424eca86f99102b4747ce3
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07776922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes