2-Bromo-3-methyl-5-chloropyridine

10201] Under nitrogen condition, 2-bromine-3-methyl-5-chioropyridine (400.00 mg, 1.94 mmol, 1.00 eq), WX1313-3-1 (465.61 mg, 2.32 mmol, 1.20 eq), sodium tert-butoxide (372.35 mg, 3.87 mmol, 2.00 eq), 1, 1?-binaphthyl-2, 2?-bis (diphenylphosphino) (241.26mg, 387.47 tmol, 0.20 eq) and tris(dibenzylideneacetone)dipalladium (177.40 mg, 193.73 tmol, 0.10 eq) were dissolved in anhydrous methylbenzene (10.00 mE). The mixture was stirred at 90 C. for 12 h. After reaction, the reaction liquid was dried by rotary evaporation to obtain the crude. The crude was purified by column chromatography (ethyl acetate: petroleum ether=1.-20%) to obtain WXO11-1. 'H NMR (400 MHz, CDC13) oeppm: 7.96 (d, J=2.00 Hz, 1H), 7.22 (s, 1H), 4.17-4.06 (m, 1H), 3.68- 3.61 (m, 1H), 3.58-3.46 (m, 2H), 3.41-3.31 (m, 1H), 2.07 (s, 3H), 1.99-1.86 (m, 1H), 1.84-1.67 (m, 2H), 1.65-1.60 (m, 1H), 1.59 (s, 9H).2.8 g (20.4 mmol) of (2-methylpyridin-4-yl)boronic acid and 6.3 g (30.6 mol / 1 .5 eq.) of General procedure: A microwave vial was charged with i-benzyl-i, 2, 5, 6-tetrahydropyridin-3-yl 1, 1, 2, 2, 3, 3 , 4, 4, 4-nonafluorobutane- 1 -sulfonate (Intermediate 4; 0.986 g, 2.093 mmol), 1-methyl-2-(4, 4, 5 , 5-tetramethyl- 1, 3 , 2-dioxaborolan-2-yl)- 1 H-indole (CAS 596819-10-2;0.565 g, 2.197 mmol) and potassium carbonate (0.868 g, 6.28 mmol) in dioxane (15 mL)/water (3.75 mL). The stirred mixture was degassed by bubbling nitrogen through it for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.121 g, 0.105 mmol) was added and the mixture was degas sed for another minute before being sealed and irradiated in amicrowave reactor at 100 C for 20 minutes. The reaction mixture was diluted with EtOAc and washed with water then brine and the organic part was loaded onto a pre-equilibrated cation exchange cartridge (SCX-2) and was eluted with EtOAc then EtOAc/[1M NH3 in MeOHj (4:1) and then EtOAc/[2M NH3 in MeOHj (4:1). The product containing fractions were combined and reduced in vacuo to afford the title compound.