Br[C:2]1[C:3]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:18](=[O:28])[C:4]=2[N:5]2[CH2:14][CH2:13][C:12]3[CH:11]=[C:10]([O:15][CH3:16])[C:9]([F:17])=[CH:8][C:7]=3[C:6]=12.C([Sn](CCCC)(CCCC)[C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)CCC>C1(C)C=CC=CC=1.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:24]([N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C:3]2[C:2]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)=[C:6]3[C:7]4[CH:8]=[C:9]([F:17])[C:10]([O:15][CH3:16])=[CH:11][C:12]=4[CH2:13][CH2:14][N:5]3[C:4]=2[C:18]1=[O:28])([CH3:27])([CH3:26])[CH3:25]To a degassed solution of 50 mg 27b and 62.3 mg 2-(tributylstannyl)thiophene in 3 mL toluene was added 12.9 mg tetrakis(triphenylphosphine)palladium(0). The mixture was stirred at reflux for 16 h. The crude reaction mixture purified by column chromatography over silica and was then triturated with diisopropyl ethyl ether/pentane (1:1) to give 38 mg 27c as a yellow solid.
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