Ethyl Acetate → 5-[(2-Phenylbutanoyl)amino]-2-(5-phenyl-2-thienyl)benzamide

HRID 503695Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[C:7]1([C:13]2[S:17][C:16](B(O)O)=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.I[C:22]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:42])[CH:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:34][CH3:35])=[CH:27][C:23]=1[C:24]([NH2:26])=[O:25].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>[C:36]1([CH:33]([CH2:34][CH3:35])[C:32]([NH:31][C:28]2[CH:29]=[CH:30][C:22]([C:16]3[S:17][C:13]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[CH:14][CH:15]=3)=[C:23]([CH:27]=2)[C:24]([NH2:26])=[O:25])=[O:42])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.5 ml of saturated aqueous sodium carbonate solution, 37 mg (0.18 mmol) of 5-phenyl-2-thiopheneboronic 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). 18 mg (30% of theory) of product are obtained.

Workup

extractionextracted three times with 50 ml of water
dry with materialThe organic phase is dried over magnesium sulfate
customThe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 10:90→95:5)
custom18 mg (30% of theory) of product are obtained

Sources & evidence

ORD record: ord-f7e3cb82195d45bc99f307a5d237b22b
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776922B2

Reaction notes

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