Reaction SMILES: FC(F)(F)S(O[C:7]1[CH2:8][C@H:9]2[C:15](=[O:16])[N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:13]3[CH:25]=[C:26]([O:31][CH2:32][CH2:33][CH2:34][O:35][C:36]4[C:37]([O:81][CH3:82])=[CH:38][C:39]5[C:45](=[O:46])[N:44]6[CH:47]=[C:48](/[CH:50]=[CH:51]/[CH2:52][NH:53][C:54]([O:56][CH2:57][CH:58]7[C:70]8[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=8[C:64]8[C:59]7=[CH:60][CH:61]=[CH:62][CH:63]=8)=[O:55])[CH2:49][C@H:43]6[C:42](=[O:71])[N:41]([CH2:72][O:73][CH2:74][CH2:75][Si:76]([CH3:79])([CH3:78])[CH3:77])[C:40]=5[CH:80]=4)[C:27]([O:29][CH3:30])=[CH:28][C:12]=3[C:11](=[O:83])[N:10]2[CH:84]=1)(=O)=O.[CH3:87][N:88]1[CH2:93][CH2:92][N:91](OB(C2C=CC=CC=2)O)[CH2:90][CH2:89]1.C(N([CH2:108][CH3:109])CC)C>C1(C)C=CC=CC=1.C(O)C.O>[CH3:82][O:81][C:37]1[C:36]([O:35][CH2:34][CH2:33][CH2:32][O:31][C:26]2[C:27]([O:29][CH3:30])=[CH:28][C:12]3[C:11](=[O:83])[N:10]4[CH:84]=[C:7]([C:109]5[CH:108]=[CH:9][C:8]([N:91]6[CH2:90][CH2:89][N:88]([CH3:87])[CH2:93][CH2:92]6)=[CH:7][CH:84]=5)[CH2:8][C@H:9]4[C:15](=[O:16])[N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:22])[CH3:23])[C:13]=3[CH:25]=2)=[CH:80][C:40]2[N:41]([CH2:72][O:73][CH2:74][CH2:75][Si:76]([CH3:78])([CH3:77])[CH3:79])[C:42](=[O:71])[C@@H:43]3[CH2:49][C:48](/[CH:50]=[CH:51]/[CH2:52][NH:53][C:54](=[O:55])[O:56][CH2:57][CH:58]4[C:59]5[CH:60]=[CH:61][CH:62]=[CH:63][C:64]=5[C:65]5[C:70]4=[CH:69][CH:68]=[CH:67][CH:66]=5)=[CH:47][N:44]3[C:45](=[O:46])[C:39]=2[CH:38]=1
Reactant: COc1cc2c(cc1OCCCOc1cc3c(cc1OC)C(=O)N1C=C(OS(=O)(=O)C(F)(F)F)C[C@H]1C(=O)N3COCC[Si](C)(C)C)N(COCC[Si](C)(C)C)C(=O)[C@@H]1CC(/C=C/CNC(=O)OCC3c4ccccc4-c4ccccc43)=CN1C2=O
Reactant: CCN(CC)CC
Reactant: CN1CCN(OB(O)c2ccccc2)CC1
Solvent: O
Solvent: Cc1ccccc1
Solvent: CCO
Product: COc1cc2c(cc1OCCCOc1cc3c(cc1OC)C(=O)N1C=C(c4ccc(N5CCN(C)CC5)cc4)C[C@H]1C(=O)N3COCC[Si](C)(C)C)N(COCC[Si](C)(C)C)C(=O)[C@@H]1CC(/C=C/CNC(=O)OCC3c4ccccc4-c4ccccc43)=CN1C2=O
Yield: 54 %

Procedure:
Mono triflate 13 (0.100 g, 0.0802 mmol, 1.0 eq.), (4-methylpiperazin-1-yl)phenylboronic acid, pinacol ester (0.023 g, 0.0762, 0.95 eq.) and triethylamine (0.051 mL, 0.369 mmol, 4.6 eq.) were solubilised in a mixture of Toluene/Ethanol/H2O [6:3:1] (4 mL) under a nitrogen atmosphere. The reaction was flushed with nitrogen for 5 minutes and palladium-tetrakistriphenylphosphine (0.9 mg, 0.000802 mmol, 0.01 eq.) was added. The reaction was then subjected to microwave irradiation at 80° C. for 5 minutes. The above reaction was repeated 3 times on 0.100 g scale. The combined reaction mixtures were concentrated under reduced pressure, and the solid residue was partitioned between H2O (180 mL) and ethyl acetate (180 mL). The aqueous layer was extracted with ethyl acetate (2×180 mL) before the combined organics were washed with brine (180 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting crude mixture was purified by flash chromatography (silica gel, 40:1 v/v DCM/MeOH to 20:1 v/v DCM/MeOH) to afford the desired product as a yellow solid (0.220 g, 54%). LC/MS (2.833 min (ES+)), m/z: 1272.53 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.77 (d, 2H, J=7.5 Hz), 7.60 (d, 2H, J=7.3 Hz), 7.43-7.39 (m, 3H), 7.35-7.30 (m, 6H), 6.95 (m, 1H), 6.90-6.87 (m, 1H), 6.34 (d, 1H, J=15.7 Hz), 5.67-5.57 (m, 1H), 5.50 (dd, 2H, J=10.1, 3.3 Hz), 4.86 (m, 1H), 4.75 (dd, 2H, J=10.1, 5.6 Hz), 4.54 (m, 2H), 4.44 (d, 2H, J=6.8 Hz), 4.31-4.21 (m, 6H), 3.96-3.87 (m, 9H), 3.81-3.73 (m, 3H), 3.71-3.62 (m, 3H), 3.31-3.20 (m, 5H), 3.10 (m, 1H), 2.87 (m, 1H), 2.58 (m, 4H), 2.43 (m, 2H), 2.36 (s, 3H), 0.97 (m, 4H), 0.01 (s, 18H).