Methods and intermediates for preparing therapeutic compounds

A process for preparing a compound of formula III:

• or a co-crystal, solvate, salt, or combination thereof, comprising:
• combining a compound of formula IV:
• or a co-crystal, solvate, salt, or combination thereof, with
• a compound of formula V:
• or a co-crystal, solvate, salt, or combination thereof, wherein R1 is B(OH)2, B(OCH(Me)CH2C(Me)2O), B((1,2-di-O)C6H4), B(OCH2C(Me)2CH2O), BF3K, B(O2CCH2N(Me)CH2CO2), or B(OC(Me)2C(Me)2O),
• a palladium catalyst selected from the group consisting of palladium(II) chloride, palladium acetate, palladium trifluoroacetate, dichloro(1,5-cyclooctadiene)palladium(II), allylpalladium(II) chloride dimer, palladium(II) acetylacetonate, (tetrakis(triphenylphosphine)palladium(0) and bis(dibenzylideneacetone)palladium(0),
• a base selected from the group consisting of potassium bicarbonate, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, potassium phosphate dibasic, potassium phosphate tribasic, sodium hydroxide, potassium hydroxide, dicyclohexylamine, N-methylmorpholine, and triethylamine, and
• a solvent selected from the group consisting of n-butyl acetate, water, di-n-butyl ether, 1,4-dioxane, 2-methyltetrahydrofuran, dimethoxyethane, toluene, xylenes, ethyl acetate, isopropyl acetate, propyl acetate, isobutyl acetate, ethanol, isopropanol, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidine, and combinations thereof, to provide the compound of formula III or a co-crystal, solvate, salt, or combination thereof.