Reaction SMILES: [CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)[C:25]([C:27]5([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]5)=[O:26])=[CH:20][C:19]=4[F:40])=[C:11]3[C:10](I)=[N:9]2)=[CH:5][CH:4]=1.[CH3:44][N:45]1[CH2:50][CH2:49][N:48]([CH2:51][C:52]2[O:53][CH:54]=[C:55]([Sn](CCCC)(CCCC)CCCC)[CH:56]=2)[CH2:47][CH2:46]1.[Br:70][C:71]1[CH:72]=[C:73]([CH2:89][N:90]2[CH2:95][CH2:94][N:93]([CH3:96])[CH2:92][CH2:91]2)[O:74][C:75]=1[Sn](CCCC)(CCCC)CCCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)[C:25]([C:27]5([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]5)=[O:26])=[CH:20][C:19]=4[F:40])=[C:11]3[C:10]([C:75]3[O:74][C:73]([CH2:89][N:90]4[CH2:95][CH2:94][N:93]([CH3:96])[CH2:92][CH2:91]4)=[CH:72][C:71]=3[Br:70])=[N:9]2)=[CH:5][CH:4]=1.[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)[C:25]([C:27]5([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]5)=[O:26])=[CH:20][C:19]=4[F:40])=[C:11]3[C:10]([C:55]3[CH:56]=[C:52]([CH2:51][N:48]4[CH2:47][CH2:46][N:45]([CH3:44])[CH2:50][CH2:49]4)[O:53][CH:54]=3)=[N:9]2)=[CH:5][CH:4]=1
Reactant: COc1ccc(Cn2nc(I)c3c(Oc4ccc(N(C(=O)C5(C(N)=O)CC5)c5ccc(F)cc5)cc4F)ccnc32)cc1
Reactant: CCCC[Sn](CCCC)(CCCC)c1oc(CN2CCN(C)CC2)cc1Br
Reactant: CCCC[Sn](CCCC)(CCCC)c1coc(CN2CCN(C)CC2)c1
Agent: Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
Solvent: C1COCCO1
Product: COc1ccc(Cn2nc(-c3coc(CN4CCN(C)CC4)c3)c3c(Oc4ccc(N(C(=O)C5(C(N)=O)CC5)c5ccc(F)cc5)cc4F)ccnc32)cc1
Product: COc1ccc(Cn2nc(-c3oc(CN4CCN(C)CC4)cc3Br)c3c(Oc4ccc(N(C(=O)C5(C(N)=O)CC5)c5ccc(F)cc5)cc4F)ccnc32)cc1
Temperature: 90 °C

Procedure:
A stirred mixture of N-(4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (35 mg, 0.0503 mmol, prepared according to Example 66, Step C) and a 14:86 mixture of 1-methyl-4-((4-(tributylstannyl)furan-2-yl)methyl)piperazine and 1-((4-bromo-5-(tributylstannyl)furan-2-yl)methyl)-4-methylpiperazine (26.0 mg, 0.0554 mmol, prepared according to Example 66, Step B) in dioxane (0.5 mL) was sparged with N2 for 2 minutes, and then PdCl2(PPh3)2 (2 mg, 0.003 mmol) was added. The reaction was heated at 90° C. for 18 hours in a sealed vessel. After cooling to ambient temperature, the crude reaction mixture was loaded directly on to a preparative TLC plate (0.5 mm thickness, Rf=0.60) eluting with 90:10 CHCl3/MeOH (containing 7N NH3). The product was isolated as an off-white solid (27 mg, 83:17 mixture of N-(4-(1-(4-methoxybenzyl)-3-(3-bromo-5-((4-methylpiperazin-1-yl)methyl)furan-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide and N-(4-(1-(4-methoxybenzyl)-3-(5-((4-methylpiperazin-1-yl)methyl)furan-3-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide). 1H-NMR (400 MHz, CDCl3) δ 9.95 (s, 1H), 8.32 (d, J=6 Hz, 1H), 8.18 (s, 1H), 7.71 (m, 1H), 7.42 (m, 4H), 7.21 (m, 2H), 7.06 (t, J=9 Hz, 2H), 6.84 (d, J=9 Hz, 2H), 6.41 (s, 1H), 6.26 (d, J=6 Hz, 1H), 5.70 (s, 2H), 3.76 (s, 3H), 3.54 (m, 2H), 2.25-2.63 (m, 8H), 2.19 (s, 3H), 1.79 (m, 2H), 1.61 (m, 2H). The mixture of products was used directly in the next step.