Reaction SMILES: [NH2:1][C:2]1[C:3]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([Br:19])[CH:13]=3)[C:10](=[O:20])[O:9][N:8]=2)=[N:4][O:5][N:6]=1.CS(O)(=O)=O.C([SiH](CC)CC)C.[CH:33]1[C:45]2[CH:44]([CH2:46][O:47][C:48](=[O:60])[NH:49][S:50]([NH:53][CH2:54][CH:55](OC)OC)(=[O:52])=[O:51])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1>C(Cl)Cl.C([SiH](CC)CC)C.C1C2C(COC(=O)NS(NCC(OC)OC)(=O)=O)C3C(=CC=CC=3)C=2C=CC=1.CCCCCCC.C(O)(C)C>[Br:19][C:14]1[CH:13]=[C:12]([N:11]2[C:10](=[O:20])[O:9][N:8]=[C:7]2[C:3]2[C:2]([NH:1][CH2:55][CH2:54][NH:53][S:50]([NH:49][C:48](=[O:60])[O:47][CH2:46][CH:44]3[C:43]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[C:37]4[C:45]3=[CH:33][CH:34]=[CH:35][CH:36]=4)(=[O:51])=[O:52])=[N:6][O:5][N:4]=2)[CH:17]=[CH:16][C:15]=1[F:18]
Reactant: Nc1nonc1-c1noc(=O)n1-c1ccc(F)c(Br)c1
Reactant: COC(CNS(=O)(=O)NC(=O)OCC1c2ccccc2-c2ccccc21)OC
Agent: CC[SiH](CC)CC
Agent: CS(=O)(=O)O
Solvent: CCCCCCC
Solvent: CC(C)O
Solvent: ClCCl
Product: O=C(NS(=O)(=O)NCCNc1nonc1-c1noc(=O)n1-c1ccc(F)c(Br)c1)OCC1c2ccccc2-c2ccccc21
Temperature: 17.5 °C
Reaction time: 72 h
Yield: 91.2 %

Procedure:
To a stirred suspension of 3-(4-amino-1,2,5-oxadiazol-3-yl)-4-(3-bromo-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (10.00 g, 29.23 mmol) in DCM (160 mL) was added methanesulfonic acid (MeSO3H, 8.46 g, 88.04 mmol) and triethylsilane (Et3SiH, 8.37 g, 71.96 mmol) at ambient temperature over 10 minutes to give a slurry. Solid 9H-fluoren-9-ylmethyl{[(2,2-dimethoxyethyl)amino]sulfonyl}carbamate (12.25 g, 30.14 mmol) was added portionwise (1 g/3-4 min; over 1 h) while maintaining the internal temperature at less than about 20° C. using a water bath. After the addition, the resulting mixture was stirred at about 13 to 22° C. for 3 days. Additional triethylsilane (Et3SiH, 0.1755 g, 1.51 mmol) and 9H-fluoren-9-ylmethyl{[(2,2-dimethoxyethy)amino]sulfonyl}carbamate (0.3082 g, 0.76 mmol) were added and the resulting mixture was stirred at ambient temperature for an additional 23 h. Isopropyl alcohol (IPA, 15 mL) was added and the resulting mixture was stirred at ambient temperature for 1 h. Heptane (100 mL) was added and the mixture was stirred at ambient temperature for an additional 2 h. The solids were collected by filtration, washed with IPA/heptane (1/5; 2×30 mL) and heptane (2×30 mL), and dried under vacuum to afford 9H-fluoren-9-ylmethyl ({[2-({4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}amino)ethyl]amino}sulfonyl)carbamate as a white solid (18.30 g, 91.1% yield). 1H NMR (500 MHz, DMSO-d6) δ 11.44 (s, 1H), 8.07 (dd, J=6.2, 2.5 Hz, 1H), 7.90 (t, J=5.6 Hz, 1H), 7.88 (d, J=7.6 Hz, 2H), 7.72 (d, J=7.0 Hz, 2H), 7.71 (ddd, J=8.9, 4.3, 2.6 Hz, 1H), 7.57 (dd, J=8.7, 8.7 Hz, 1H), 7.40 (t, J=7.4 Hz, 2H), 7.31 (td, J=7.4, 1.0 Hz, 2H), 6.55 (t, J=6.0 Hz, 1H), 4.35 (d, J=7.3 Hz, 2H), 4.25 (t, J=7.2 Hz, 1H), 3.39 (q, J=6.4 Hz, 2H), 3.15 (q, J=6.3 Hz, 2H); 13C NMR (126 MHz, DMSO-d6) δ 159.03 (d, J=248.7 Hz), 156.61 (s), 155.22 (s), 151.55 (s), 148.67 (s), 143.29 (s), 140.68 (s), 133.82 (s), 133.39 (s), 130.05 (d, J=8.5 Hz), 128.54 (d, J=3.2 Hz), 127.73 (s), 127.07 (s), 125.24 (s), 120.11 (s), 117.42 (d, J=24.0 Hz), 108.19 (d, J=22.5 Hz), 66.70 (s), 46.17 (s), 43.34 (s), 40.79 (s) ppm; 19F NMR (376 MHz, DMSO-d6) δ −103.99-−107.39 (m) ppm.