[CH3:1][NH:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1CCN2C(=NCCC2)CC1.C[CH2:49][O:50]CC>CC(N(C)C)=O>[CH3:1][N:2]([C:49](=[O:50])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
A pressure vessel (Fisher-Porter bottle) equipped with a Teflon coated stir bar, a gas inlet, a pressure gauge, and a pressure release valve was charged with N-methylbenzamide (242 mg, 1.79 mmol), iodobenzene (200 μl, 1.29 mmol), PdCl2L2 (76 mg, 0.107 mmol), triphenylphosphine (56 mg, 0.214 mmol) and DMAc (3.4 ml) and heated (115° C.) under one atmosphere of CO until the reactants had dissolved. DBU (320 μl, 2.14 mmol) was then introduced into the reaction mixture and the reactor charged to 40 psi with CO. After 23 hours, the reactor was cooled to room temperature, depressurized, and the reaction mixture diluted (50 ml) with ether and extracted (3×50 ml) with water. The ether layer was dried over MgSO4 and concentrated to give a red oil which was chromatographed on silica gel (2:1, hexane:ethyl acetate) to give 30 mg product (7%).
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