Reaction SMILES: [Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18](I)[C:17]([O:21][CH3:22])=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[Cl:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[C:25]=1[C@H:33]([C:35]1[C:43]2[C:38](=[N:39][CH:40]=[C:41](B3OC(C)(C)C(C)(C)O3)[CH:42]=2)[NH:37][CH:36]=1)[CH3:34].C(=O)([O-])[O-].[K+].[K+].[F-].[K+].ClCCl.N#N.Cl>O1CCOCC1.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.O1CCOCC1.O>[Cl:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[C:25]=1[C@H:33]([C:35]1[C:43]2[C:38](=[N:39][CH:40]=[C:41]([C:18]3[C:17]([O:21][CH3:22])=[N:16][N:15]([C@H:12]4[CH2:11][CH2:10][C@H:9]([OH:8])[CH2:14][CH2:13]4)[CH:19]=3)[CH:42]=2)[NH:37][CH:36]=1)[CH3:34]
Reactant: COc1ccc(F)c(Cl)c1[C@@H](C)c1c[nH]c2ncc(B3OC(C)(C)C(C)(C)O3)cc12
Reactant: COc1nn([C@H]2CC[C@H](O[Si](C)(C)C(C)(C)C)CC2)cc1I
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: Cl
Agent: N#N
Solvent: C1COCCO1
Solvent: ClCCl
Solvent: O
Product: COc1ccc(F)c(Cl)c1[C@@H](C)c1c[nH]c2ncc(-c3cn([C@H]4CC[C@H](O)CC4)nc3OC)cc12
Temperature: 100 °C

Procedure:
A solution of 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-3-methoxy-1H-pyrazole (0.088 g, 0.20 mmol), 3-[(S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.0699 g, 0.162 mmol), potassium carbonate (0.0673 g, 0.487 mmol), potassium fluoride (0.00943 g, 0.162 mmol) in previously degassed dioxane/H2O (5:1) (4.00 mL) was charged with Pd(PPh3)4 (0.00937 g, 0.00811 mmol) and was evacuated and charged with N2 (3×) and heated under microwave conditions [Biotage, 100° C., 40 min, high absorption]. The reaction mixture was charged with an additional amount of Pd(PPh3)4 (0.00938 g, 0.00812 mmol) and 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-3-methoxy-1H-pyrazole (0.0354 g, 0.0812 mmol) evacuated and charged with N2 gas (3×) and heated under microwave conditions [Biotage, 100° C., 30 min, high absorption]. The reaction mixture was charged with 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride.dichloromethane (0.00663 g, 0.00812 mmol) and evacuated and charged with N2 and heated under microwave conditions [Biotage, 100° C., 30 min, high absorption]. The reaction was stopped and charged with 4 M of HCl in 1,4-dioxane (0.500 mL) and heated under microwave conditions [Biotage, 60° C., 15 min, high absorption]. The reaction mixture was partitioned between CHCl3 and sat. NaHCO3 and separated. The aqueous was re-extracted with CHCl3 (3×) and the combined organic fractions were washed with brine (1×), dried over Na2SO4, filtered and concentrated in vacuo resulting in a crude dark brown oil. This was purified by chromatography on silica gel [ISCO Combiflash, 12 g gold cartridge, eluting with 2% MeOH in DCM→10% MeOH in DCM] resulting in the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=1.42-1.54 (m, 2H), 1.80 (d, J=7.3 Hz, 3H), 1.83-1.94 (m, 1H), 2.05-2.18 (m, 3H), 3.59-3.71 (m, 3H), 3.94 (s, 2H), 3.95-4.04 (m, 1H), 5.09 (q, J=7.0 Hz, 1H), 6.89 (dd, J=4.3, 8.8 Hz, 1H), 7.11 (dd, J=8.8, 8.8 Hz, 1H), 7.28 (d, J=1.3 Hz, 1H), 7.74 (s, 1H), 7.85 (s, 1H), 8.29 (d, J=1.8 Hz, 1H). MS (ES+): m/z 499.18 (75), 501.14 (25) [MH+]. HPLC: tR=2.56 min (vvnonpolar—5 min, ZQ3).