Processes for preparing JAK inhibitors and related intermediate compounds

A process of preparing a compound of Formula XII:

• comprising reacting a compound of Formula X:
• with a compound of Formula XIII:
• in the presence of a palladium catalyst, base, and a solvent, to form a compound of Formula XII;
• wherein:
• X2 is a tosylate group, a triflate group, iodo, chloro, or bromo;
• and
• Rc and Rd are each independently H or C1-6 alkyl;
• or
• Rc and Rd, together with the oxygen atoms to which they are attached and the boron atom to which the oxygen atoms are attached, form a 5- to 6-membered heterocyclic ring, which is optionally substituted with 1, 2, 3, or 4 C14 alkyl groups;
• P1 is independently a protecting group;
• and
• P2 is a protecting group selected from the group consisting of 1-(ethoxy)ethyl, p-methoxybenzyl, triphenylmethyl, diphenylmethyl, hydroxymethyl, methoxymethyl, and t-butyldimethylsilylmethyl.