Reaction SMILES: I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[N:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:50]=[CH:49][C:36]([NH:37][C:38]3[O:39][C:40]4[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][C:41]=4[N:42]=3)=[CH:35][CH:34]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C@H:12]3[CH2:17][CH2:16][C@@H:15]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[CH2:14][CH2:13]3)[N:3]=[C:2]([C:33]3[CH:50]=[CH:49][C:36]([NH:37][C:38]4[O:39][C:40]5[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][C:41]=5[N:42]=4)=[CH:35][CH:34]=3)[C:10]=12
Reactant: CN1CCN(C2CCC(n3nc(I)c4c(N)ncnc43)CC2)CC1
Reactant: CC1(C)OB(c2ccc(Nc3nc4cc(C#N)ccc4o3)cc2)OC1(C)C
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+]
Solvent: O
Solvent: COCCOC
Product: CN1CCN([C@H]2CC[C@@H](n3nc(-c4ccc(Nc5nc6cc(C#N)ccc6o5)cc4)c4c(N)ncnc43)CC2)CC1
Temperature: 80 °C
Reaction time: 16 h
Yield: 79.4 %

Procedure:
A mixture of 3-iodo-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.15 g, 0.00034 mol), 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]-1,3-benzoxazole-5-carbonitrile (0.153 g, 0.000425 mol), tetrakis(triphenylphosphine)palladium (0.028 g, 0.0000238 mol) and sodium carbonate (0.090 g, 0.00085 mol) in ethylene glycol dimethyl ether (3 mL) and water (1 mL) was heated at 80° C. for 16 hours. Additional 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]-1,3-benzoxazole-5-carbonitrile (0.072 g, 0.0002 mol), tetrakis(triphenylphosphine)palladium (0.012 g, 0.000010 mol, 0.03 eq.) were added, and the mixture was stirred at 80° C. for 16 hours under atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature, and the solvent was removed under the reduced pressure. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water, saturated aqueous sodium bicarbonate solution, and brine, and dried over magnesium sulfate. The solvents were evaporated under the reduced pressure, and the residue was purified by flash column chromatography on silica using 2% aqueous ammonium hydroxide solution/5%-20% methanol/dichloromethane as a mobile phase. The solvent was removed under reduced pressure, and the residue was purified by RP-HPLC (Hypersilprep HS C18, 8 μm, 250×21.1 mm; 5%-50% over 30 min with 0.1 M ammonium acetate, 21 mL/min) to give cis-2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}anilino)-1,3-benzoxazole-5-carbonitrile (0.15 g, 0.00027 mol). 1H NMR (DMSO-d6 400 MHz) δ 11.25 (s, 1H), 8.53 (s, 1H), 8.00 (s, 1H), 7.95 (d, 2H), 7.70(m, 4H), 4.80 (br, 1H), 2.49 (s, 3H), 2.20 (br, 8H), 2.10 (br, 3H), 1.75 (br, 2H), 1.60 (br, 4H). RP-HPLC (Delta Pak C18, 5 μm, 300 A, 15 cm; 5%-95% acetonitrile-0.1M ammonium acetate over 10 min, 1 mL/min) Rt 9.2 min. MS: MH+ 549.