Reaction SMILES: [C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20](Cl)[C:19]3[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=3[C:17]=2[F:34])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35]([C:37]1[CH:48]=[CH:47][C:40]2[S:41][C:42](B(O)O)=[CH:43][C:39]=2[CH:38]=1)#[N:36]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O.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:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20]([C:42]3[S:41][C:40]4[CH:47]=[CH:48][C:37]([C:35]#[N:36])=[CH:38][C:39]=4[CH:43]=3)[C:19]3[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=3[C:17]=2[F:34])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
Reactant: CC(C)(C)OC(=O)N[C@H]1COCC[C@H]1Nc1nc(Cl)c2c(c1F)CN(C(=O)OC(C)(C)C)C2=O
Reactant: N#Cc1ccc2sc(B(O)O)cc2c1
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: O=C([O-])[O-]
Solvent: C1COCCO1
Solvent: CCOC(C)=O
Product: CC(C)(C)OC(=O)N[C@H]1COCC[C@H]1Nc1nc(-c2cc3cc(C#N)ccc3s2)c2c(c1F)CN(C(=O)OC(C)(C)C)C2=O

Procedure:
A solution of tert-butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (100 mg, 0.200 mmol), 5-cyanobenzo[b]thiophen-2-ylboronic acid (40.5 mg, 0.200 mmol) and tetrakis(triphenylphosphine)palladium(0) (231 mg, 0.200 mmol) in dioxane and saturated aqueous Na2CO3 (3:5, 6 mL) was heated to 120° C. in a microwave for 30 minutes. The reaction mixture was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated and the aqueous layer was washed with EtOAc (50 mL). The organic layers were combined, dried over Na2SO4, and the solvent was removed in vacuo to give the intermediate, tert-butyl 6-(((3R,4R)-3-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-4-yl)amino)-4-(5-cyanobenzo[b]thiophen-2-yl)-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate. The intermediate was dispersed in TFA and DCM (1:1, 10 mL) and the mixture was stirred at room temperature for 60 minutes. The mixture was concentrated, reconstituted in MeOH and DCM (10.0 mL) and purified via preparative HPLC eluting with a gradient of 10-25% ACN (0.035% TFA) and H2O (0.05% TFA). The collected fractions were combined and diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was separated and the aqueous layer was washed with EtOAc (50 mL). The organic layers were combined, dried over Na2SO4, and the solvent was removed in vacuo to give the title compound (26 mg, 31%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.78 (dd, J=13.42, 4.15 Hz, 1H), 1.87-2.05 (m, 1H), 3.17-3.25 (m, 1H), 3.45-3.57 (m, 1H), 3.67 (d, J=10.25 Hz, 1H), 3.80 (br s, 1H), 3.91 (d, J=11.23 Hz, 1H), 4.26 (d, J=4.39 Hz, 1H), 4.43 (s, 2H), 7.00 (d, J=6.35 Hz, 1H), 7.72 (dd, J=8.30, 1.46 Hz, 1H), 8.20 (d, J=8.30 Hz, 1H), 8.47 (d, J=1.46 Hz, 1H), 8.61 (s, 1H), 9.50 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C21H18FN5O2S, 424. found, 424.