Reaction SMILES: [C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39](Br)[C:38]2=[N:43][C:35]3=[C:36](Br)[N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[C:26]([CH3:47])[C:27]([F:46])=[CH:28][C:29]=2[C:30]2[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:52]B(O)O.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+].O[Li].O>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2].[Pd]>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([CH3:52])[C:38]2=[N:43][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[C:26]([CH3:47])[C:27]([F:46])=[CH:28][C:29]=2[C:30]2[CH:45]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]
Reactant: COC(=O)[C@@H](OC(C)(C)C)c1c(C)c(Br)c2nc3c(Br)n2c1N1CCC(C)(CC1)OCCCC[C@H](C)Oc1cc(C)c(F)cc1-c1cccc-3c1
Reactant: CB(O)O
Agent: [Pd+2]
Agent: [Pd]
Agent: CC(=O)[O-]
Solvent: CN(C)C=O
Solvent: O
Product: Cc1cc2c(cc1F)-c1cccc(c1)-c1cn3c(c([C@H](OC(C)(C)C)C(=O)O)c(C)c(C)c3n1)N1CCC(C)(CC1)OCCCC[C@H](C)O2
Temperature: 25 °C
Reaction time: 6 h
Yield: 24.4 %

Procedure:
A solution of methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (21 mg, 0.025 mmol, 1 equiv), methylboronicacid (6 mg, 0.101 mmol, 4 equiv), Pd(OAc)2 (0.6 mg, 0.003 mmol, 0.1 equiv), Sphos (2 mg, 0.005 mmol, 0.2 equiv), and Cs2CO3 (12 mg, 0.038 mmol, 1.5 equiv) in DMF (0.46 mL) and water (0.046 mL) was heated to 80° C. for 20 h. More methylboronicacid (6 mg, 0.101 mmol, 4 equiv) and Cs2CO3 (12 mg, 0.038 mmol, 1.5 equiv) were added. After 6 h, remove from heat. Upon cooling to ambient temperature, the reaction was diluted with EtOAc and washed with water. The EtOAc was dried (Na2SO4) and concentrated in vacuo. The crude product was taken up in MeOH (2 mL) was added 10% Pd/C (5 mg, 0.005 mmol, 0.2 equiv). The reaction was then stirred under a balloon of H2 for 1 h. The reaction was then filtered through Celite eluting with MeOH. The filtrate was then concentrated in vacuo. The crude hydrogenation product was taken up in 10:1 MeOH:water (1 mL) and LiOH.H2O (32 mg, 0.759 mmol, 30 equiv) was added. The reaction was heated to 70° C. for 3 h. Upon cooling to ambient temperature, the reaction was filtered and purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient: 70-100% B over 15 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min to provide the product (4.1 mg, 24%). 1H NMR (500 MHz, DMSO-d6) δ 8.13 (d, J=1.8 Hz, 2H), 7.97 (s, 1H), 7.51 (t, J=8.1 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 7.15 (d, J=10.3 Hz, 1H), 7.09 (d, J=6.6 Hz, 1H), 5.80 (br. s., 1H), 4.62 (br. s., 1H), 3.84 (t, J=10.3 Hz, 1H), 3.60-3.52 (m, 1H), 3.44 (br. s., 3H), 2.64 (d, J=9.2 Hz, 1H), 2.47 (s, 3H), 2.30 (br. s., 3H), 2.29 (br. s., 3H), 1.93-1.51 (m, 10H), 1.20 (s, 3H), 1.14 (s, 9H), 1.08 (d, J=6.2 Hz, 3H); LCMS (ESI, M): 671.4.