Reaction SMILES: Br[C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]([C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([C:21]([NH:23][CH2:24][C:25]3[C:26]([NH:38][CH:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[C:27]4[CH:35]=[N:34][N:33]([CH2:36][CH3:37])[C:28]4=[N:29][C:30]=3[CH2:31][CH3:32])=[O:22])[CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:45][C@H:46]1[CH2:51][N:50]([CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[C:55](B3OC(C)(C)C(C)(C)O3)[CH:54]=2)[CH2:49][CH2:48][N:47]1C(OC(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+]>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>[CH2:36]([N:33]1[C:28]2=[N:29][C:30]([CH2:31][CH3:32])=[C:25]([CH2:24][NH:23][C:21]([C:16]3[CH:17]=[C:18]([CH3:20])[CH:19]=[C:14]([C:12]([NH:11][CH2:10][C:4]4[CH:3]=[C:2]([C:55]5[CH:56]=[CH:57][CH:58]=[C:53]([CH2:52][N:50]6[CH2:49][CH2:48][NH:47][C@@H:46]([CH3:45])[CH2:51]6)[CH:54]=5)[C:7]([O:8][CH3:9])=[CH:6][CH:5]=4)=[O:13])[CH:15]=3)=[O:22])[C:26]([NH:38][CH:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[C:27]2[CH:35]=[N:34]1)[CH3:37]
Reactant: C[C@H]1CN(Cc2cccc(B3OC(C)(C)C(C)(C)O3)c2)CCN1C(=O)OC(C)(C)C
Reactant: CCc1nc2c(cnn2CC)c(NC2CCOCC2)c1CNC(=O)c1cc(C)cc(C(=O)NCc2ccc(OC)c(Br)c2)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: [K+]
Product: CCc1nc2c(cnn2CC)c(NC2CCOCC2)c1CNC(=O)c1cc(C)cc(C(=O)NCc2ccc(OC)c(-c3cccc(CN4CCN[C@@H](C)C4)c3)c2)c1

Procedure:
In an alternate process for the preparation of the title compound, N-{[3-bromo-4-(methyloxy)phenyl]methyl}-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-5-methyl-1,3-benzenedicarboxamide (40 mg, 0.060 mmol), 1,1-dimethylethyl (2S)-2-methyl-4-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1-piperazinecarboxylate (25.10 mg, 0.060 mmol), potassium carbonate (24.99 mg, 0.181 mmol), and Pd(Ph3P)4 (3.48 mg, 3.01 μmol) were added to a 0.5-2 mL Biotage microwave vial in 1,4-dioxane (1.5 mL) and water (0.5 mL). The vial was capped and the mixture was heated under microwave at normal power in the Emrys Optimizer at 100° C. for 15 min. The crude product was partitioned between EtOAc (30 mL) and water (10 mL). The phases were separated, and the organic phase washed with brine, dried over anhydrous Na2SO4 filtered and concentrated to give a crude intermediate. It was taken up in DCM (1.8 mL) and treated with trifluoroacetic acid (0.2 mL). The mixture was stirred under argon for 5 hours. Solvents were pumped off and the residue taken up in DMSO and purified on the Gilson with the TFA system. Evaporation of the appropriate purified fractions gave the desired product as a TFA salt. This was converted to the free base by taking the residue up in EtOAc (30 mL) and 2.5 N NaOH (5 mL). The phases were separated, the organic phase washed with 2.5 N NaOH (3×5 mL) and then with brine (2×5 mL). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-5-methyl-N′-[(6-(methyloxy)-3′-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-1,3-benzenedicarboxamide as a white solid (30.07 mg, 63.3%). LC-MS m/z 773 (M+H)+; mp 121-123° C.