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Example 1

The Iodo compound (308 mg, 0.513 mmol), the boronic ester (194 mg, 0.641 mmol), K3PO4 (327 mg, 1.539 mmol), XPhos (14.67 mg, 0.031 mmol), and Pd2(dba)3 (14.09 mg, 0.015 mmol) were combined in a microwave vial. The tube was purged with N2, after which time was added dioxane (3 mL) and H2O (0.5 mL) The reaction was irradiated in a microwave reactor at 120 C for 10 min. Additional boronic ester (50 mg) was added and the mixture was irradiated at 120 C for another 10 min. The mixture was then treated with aq 1N NaOH and extracted with EtOAc (50 mL). The org layer was dried (MgSO4), concentrated, and purified by silica gel chromatography (20% MeOH/DCM) to provide the product as a dark yellow solid. [177 mg, 0.272 mmol] [WO2012129338, page 69]

Example 2

To a solution of the Iodo compound (1.0 g, 1.66 mmol) and the boronic acid (392 mg, 2.49 mmol) in DMF (10 mL) was added K3PO4 (704 mg, 3.32 mmol). The mixture was purged with N2 for 15 min, after which time Pd(PPh3)4 (176 mg, 0.152 mmol) was added and the mixture was stirred at 85 C for 5 h. The mixture was then poured in ice cold H2O (50 mL) and extracted with EtOAc. The combined organics were washed with H2O, dried, concentrated, and purified by silica gel chromatography (15% EtOAc/hexane) to provide the product as a brown solid. [0.52 g, 53.3%] [WO2012129338, page 79]

Example 3

A suspension of the bromide (400 mg, 1.05 mmol), the boronic acid (208 mg, 1.65 mmol), Pd2(dba)3(96 mg, 0.1 mmol), XPhos (148 mg, 0.3 mmol), and Na2CO3 (112 mg, 1.05 mmol) in ACN/H2O (4:1) was heated at 90 C for 30 min. The reaction mixture was diluted with EtOAc (10 mL), the org layer was separated, dried (Na2SO4), and concentrated in vacuo. The crude was purified by flash chromatography (9:1 CHCl3/MeOH) to provide the product. [20%] [WO2010038081, page 109]

Example 4

A mixture of the SM (400 mg, 1.41 mmol), bis(pinacolato)diboron (1 g, 3.94 mmol), XPhos (135 mg, 0.28 mmol), Pd(OAc)2 (16 mg, 0.06 mmol), and TEA (570 mg, 5.6 mmol) in dioxane (20 mL) was degassed and refluxed at 100 C for 20 min under N2. The solvent was removed in vacuo, the residue diluted with DCM (20 mL), washed with H2O (2 x 20 mL), the brine. The org layer was dried (Na2SO4), concentrated, and recrystallized with DCM/hexane to provide the product. [300 mg] [WO2010038081, page 129]

Example 5

A solution of the SM (1.0 equiv), KOAc (3.0 equiv), bis(pinacolato)diboron (2.0 equiv), tricyclohexylphosphine (0.8 equiv), and Pd2(dba)3(0.2 equiv) in dioxane (0.06 M) was heated at 135 C in a microwave reactor for 20 min. The reaction mixture was filtered through a 1 uL HPLC filter, concentrated, and dried to provide the product which was used without further purification. [WO2010026121, page 36]

Example 6

The boronic ester (0.043 g, 0.16 mmol), the bromide (0.10 g, 0.16 mmol), and dioxane (1.6 mL) were combined to give a yellow suspension. A solution of Cs2CO3 (0.134 g, 0.411 mmol) in H2O (0.4 mL) was added, then N2 was bubbled through the mixture. Pd(Ph3)2Cl2 (0.008 g, 0.012 mmol) was added and the mixture was flushed again with N2. The reaction mixture was stirred at 75 C for 18 h. The mixture was concentrated and the resulting residue was purified by silica gel column chromatography (20-70% EtOAc/DCM) to provide the product. [0.072 g, 66%] [WO2012149280, page 80]