Reaction SMILES: Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[NH:16][C:15]([C@@H:17]3[CH2:21][C@H:20]([CH3:22])[CH2:19][N:18]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[N:14][C:13]=1[Cl:30])[CH:6]=[CH:5]2.[CH3:31][C@@H:32]1[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]2[NH:45][C:46]([C:49]3[CH:54]=[CH:53][C:52](B4OC(C)(C)C(C)(C)O4)=[CH:51][CH:50]=3)=[CH:47][N:48]=2)[CH2:33]1.C([O-])(O)=O.[Na+]>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:40]([O:39][C:37]([N:35]1[CH2:36][C@@H:32]([CH3:31])[CH2:33][C@H:34]1[C:44]1[NH:45][C:46]([C:49]2[CH:50]=[CH:51][C:52]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[CH:8]=[C:7]([C:12]3[NH:16][C:15]([C@@H:17]5[CH2:21][C@H:20]([CH3:22])[CH2:19][N:18]5[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])=[N:14][C:13]=3[Cl:30])[CH:6]=[CH:5]4)=[CH:53][CH:54]=2)=[CH:47][N:48]=1)=[O:38])([CH3:41])([CH3:42])[CH3:43]
Reactant: C[C@H]1C[C@@H](c2nc(Cl)c(-c3ccc4cc(Br)ccc4c3)[nH]2)N(C(=O)OC(C)(C)C)C1
Reactant: C[C@H]1C[C@@H](c2ncc(-c3ccc(B4OC(C)(C)C(C)(C)O4)cc3)[nH]2)N(C(=O)OC(C)(C)C)C1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: O=C([O-])O
Agent: [Na+]
Product: C[C@H]1C[C@@H](c2ncc(-c3ccc(-c4ccc5cc(-c6[nH]c([C@@H]7C[C@H](C)CN7C(=O)OC(C)(C)C)nc6Cl)ccc5c4)cc3)[nH]2)N(C(=O)OC(C)(C)C)C1
Temperature: 85 °C
Reaction time: 14 h
Yield: 78.1 %

Procedure:
Pd(Ph3P)4 (27.1 mg, 0.023 mmol) was added to a nitrogen purged suspension of (2S,4S)-tert-butyl 2-(5-(6-bromonaphthalen-2-yl)-4-chloro-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate, (230 mg, 0.469 mmol), (2S,4S)-tert-butyl 4-methyl-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (234 mg, 0.515 mmol) and NaHCO3 (197 mg, 2.34 mmol) in an argon-degassed solution of DME (4 mL) and water (1 mL). The pressure vessel was charged with argon, sealed, and immersed into a pre-heated oil bath (85° C.) and stirred for 14 h. The mixture was diluted with EtOAc (Note: THF and MeOH were added to aid dissolution) and washed with sat′d NaHCO3 soln, brine, dried (Na2SO4), filtered and concentrated. The residue was purified utilizing a Thompson 90 g SiO2 column (Gradient elution 5% to 100% B for 2 L and hold for 0.5 L Solvent B=ethyl acetate and Solvent A=hexanes) to yield (2S,4S)-tert-butyl 2-(5-(6-(4-(2-((2S,4S)-1-(tert-butoxycarbonyl)-4-methylpyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-4-chloro-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate (270 mg, 70%) as a foam. For the purpose of characterization approx. 20 mg was dissolved in MeOH (up to 2 mL) and subject to prep HPLC vial (0 to 100% B over a 30 min gradient at 40 ml/min) using a PHENOMENEX® Luna column (30×100 mm, S10) where B=95% CH3CN-5% H2O-10 mM NH4OAc and A=5% CH3CN-95% H2O-10 mM NH4OAc. LC-MS retention time 3.90 min; calcd. for C42H50ClN6O4: 737.36 m/z. found 737.43 [M+H]. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min and an analysis time of 5 min where Solvent A was 5% methanol/95% water/0.1% TFA and Solvent B was 95% methanol/5% water/0.1% TFA. MS data was determined using a MICROMASS® Platform for LC in electrospray mode. 1H NMR (500 MHz, MeOD) δ ppm 8.21 (s, 1H), 8.16 (s, 1H), 8.03 (d, J=8.6 Hz, 1H), 7.99 (d, J=8.6 Hz, 2H), 7.91-7.81 (m, 6H), 7.42 (s, 1H), 4.86 (under MeOH, 1H), 4.80-4.877 (m, 1H), 3.82-3.77 (m, 2H), 3.20 (t, J=10.4 Hz, 2H), 2.52-2.47 (m, 2H), 2.37-2.34 (m, 2H), 1.83-1.73 (m, 2H), 1.46/1.26/1.23 (s, 18H), 1.16 (m, 6H).