Processes and intermediates for producing azaindoles

A process for preparing a compound of Formula 4:

• wherein:
• R1 is —H, —Cl or —F;
• R2 is —H or —F;
• R3 is —C1-4 aliphatic optionally substituted with 1-5 occurrences of R5;
• R4 is —C1-2 alkyl optionally substituted with 1-3 occurrences of R5;
• or
• R3 and R4 are taken together to form a 3-7 membered carbocyclic or heterocyclic saturated ring optionally substituted with 1-5 occurrences of R5;
• each R5 is independently selected from halogen, —OCH3, —OH, —NO2, —NH2, —SH, —SCH3, —NHCH3, —CN, or unsubstituted —C1-2 aliphatic, or
• two R5 groups, together with the carbon to which they are attached, form a cyclopropyl ring;
• comprising the step of:
• ia) reacting a compound of Formula 1 with a hydrochloride salt of a compound Formula 2,
• in the presence of water, an organic solvent, a base, and a palladium catalyst selected from
• or any combination thereof,
• to generate a compound of Formula 3, and
• ii) deprotecting the compound of Formula 3 to generate the compound of Formula 4.