Process for making M1 receptor positive allosteric modulators

A process for the preparation of a compound of formula I:

• or a pharmaceutically acceptable salt thereof,
• wherein R1 is C1-6 alkyl, or C6-10 aryl
• comprising introducing an alcohol protecting group (APG) onto a compound of Formula 8
• to make a compound of Formula 9:
• coupling the compound of Formula 9 with a compound of Formula 10
• in the presence of a first palladium catalyst complex to make a compound of Formula 11, wherein X is a metal-containing moiety and Y is a leaving group,
• alkylating the compound of structural Formula 11 using a alkylating reagent to provide a compound of Formula 12:
• by way of step (1) or step (2) wherein:
• step (1) comprises adding the alkylating reagent to the reaction mixture comprising the compound of Formula 11 without further isolation to make a compound of Formula 12, or step (2) comprises isolating the compound of Formula 11 and reacting it with the alkylating reagent in the presence of a first palladium catalyst complex to provide a compound of Formula 12, and deprotecting the alcohol protecting group in the compound of Formula 12 and isolating a compound of Formula I.