Process for Preparing 1-([3R,4S)-4-Cyanotetrahydropyran-3-YL]-3-[(2-fluoro-6-Methoxy-4-Pyridyl)Amino]Pyrazole-4-Carboxamide

A process for making a compound of Formula (XII),

• wherein R is I,
• comprising
• a. reacting a compound of Formula (IX)
• with iodine and a lithium amide base, preferably lithium/TMP, to yield a compound of Formula (X)
• and
• b. converting the compound of Formula (X) to the compound of Formula (XII).

A process for making a compound of Formula (XII),

• wherein R is Br,
• comprising
• a. reacting a compound of Formula (VII)
• with an iridium catalyst and bis(pinacolato)diboron to yield a compound of Formula (VIII)
• and
• b. converting the compound of Formula (VIII) to the compound of Formula (XII).

A process for making a compound of Formula (VI)

• wherein R1 is C1-C4 alkyl, preferably C1-C2 alkyl, most preferably ethyl comprising
• a. reacting a compound of Formula (II)
• with
• i. Hydrogen cyanide or an equivalent thereof such as TMSCN and
• ii. POCl3 or SOCl2
• to yield a compound of Formula (III)
• and
• b. converting the compound of Formula (III) to the compound of Formula (VI).