Reaction SMILES: Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[I-].[Na+].C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1.[C:47]1([C:53]#[CH:54])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>[Zn].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.C1COCC1.CCOC(C)=O.CS(C)=O>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([C:54]#[C:53][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:3]=1)=[O:15]
Reactant: Cc1cc(C)c(CNC(=O)c2cc(Cl)nc3c2cnn3C(C)C)c(=O)[nH]1
Reactant: C#Cc1ccccc1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: [I-]
Agent: [Na+]
Solvent: CCOC(C)=O
Solvent: C1CCC2=NCCCN2CC1
Solvent: CS(C)=O
Product: Cc1cc(C)c(CNC(=O)c2cc(C#Cc3ccccc3)nc3c2cnn3C(C)C)c(=O)[nH]1
Temperature: 90 °C
Reaction time: 3 h

Procedure:
To a 10 mL microwave vial were sequentially added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.125 g, 0.334 mmol), sodium iodide (10.02 mg, 0.067 mmol) and zinc (4.37 mg, 0.067 mmol), DMSO (2.5 mL), triethylamine (0.093 mL, 0.669 mmol) and DBU (0.101 mL, 0.669 mmol). The stirring suspension was degassed with nitrogen for 5 min., wherein an emulsion had formed. Added next were phenylacetylene (0.110 mL, 1.003 mmol) and Pd(Ph3P)4 (0.039 g, 0.033 mmol). The sealed reaction mixture was placed onto a heat block, stirred at 90° C. for 3 hr, and then allowed to cool to room temperature overnight. The contents were poured onto water and 20% THF/EtOAc, stirred, and the layers separted. The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The filter pad was washed with additional EtOAc. The combined filtrates were concentrated in vacuo to a yellow/orange residue that was dried on hi-vac pump. The crude solid was then pre-adsorbed onto silica gel and purified by silica gel chromatography (dry loaded, eluent: 5-80% gradient of DCM and chloroform containing 10% 2M Ammonia (in methanol)). The isolated product was obtained as a yellow solid which was then further purified by reverse phase HPLC (mobile phase: 20-90% ACN in H2O, 0.1% TFA, Gradient time: 8 min). The isolated solid was dissolved in 10% MeOH/CH2Cl2 and treated with 0.6 g of Silicycle carbonate resin for 30 min. The contents were filtered through Celite and the filter pad washed with additional 10% MeOH/CH2Cl2. The combined filtrates were concentrated in vacuo to afford a solid which was dried in vacuum oven for 18 hr. The final product was collected as 0.045 g (30%). LCMS E-S (M+H)=440.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (d, J=6.82 Hz, 6H), 2.13 (s, 3H), 2.21 (s, 3H), 4.37 (d, J=4.80 Hz, 2H), 5.18-5.33 (m, 1H), 5.90 (s, 1H), 7.45-7.56 (m, 3H), 7.64-7.73 (m, 2H), 7.86 (s, 1H), 8.42 (s, 1H), 8.92 (t, J=4.80 Hz, 1H), 11.55 (br. s., 1H).