Sodium Carbonate → N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide

HRID 133546

Reaction equation

[C:1]([C:9]1[CH:13]=[C:12](Br)[S:11][C:10]=1[NH:15][C:16](=[O:18])[CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([C:9]1[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:11][C:10]=1[NH:15][C:16](=[O:18])[CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred solution of 0.448 g (1.38 mmol) of N-(3-benzoyl-5-bromo-thiophen-2-yl) acetamide in 20 ml toluene and 10 ml EtOH was degassed with argon. Tetrakis-(triphenylphosphine) palladium (0) (0.320 g, 0.27 mmol), phenyl boronic acid (0.194 g, 1.59 mmol) and 20 ml of an aqueous solution of Na2CO3 1N were added. The mixture was heated at 90° C. for 1 hour before cooling down to RT, filtered through Celite and concentrated. The mixture was extracted with ethyl acetate and aq. NaHCO3. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 6:1) afforded 0.393 g (88%) N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide as a light yellow solid. ES-MS m/e (%): 322 (M+H+, 100).

Workup

temperaturebefore cooling down to RT
filtrationfiltered through Celite
concentrationconcentrated
extractionThe mixture was extracted with ethyl acetate and aq. NaHCO3
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-05943aea103c471bbd9ee1e2aee9c135
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Linked notes

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