Process for the synthesis C-2, C-3 substituted N-alkylated indoles useful as CPLA2 inhibitors

A compound of formula 3:

• wherein:
• R1, R2, R3, and R4 each is independently selected from the group consisting of H, halogen, —CN, —CHO, —CF3, —OCF3, —OH, —NO2, —C1-6 alkyl, —C1-6 alkoxy, —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)2, and —NHC(O)—C1-6 alkyl;
• and
• R5 is selected from the group consisting of H and —C(O)O—C1-6 alkyl.

A method for making a compound of formula 4:

• comprising the step of reacting compounds of formulas 2 and 3:
• wherein:
• R1, R2, R3, and R4 each are independently selected from the group consisting of H, halogen, —CN, —CHO, —CF3, —OCF3, —OH, —NO2, —C1-6 alkyl, C1 alkoxy, —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)2, and —NHC(O)—C1-6 alkyl;
• and
• R5 is selected from the group consisting of H and —C(O)O—C1-6 alkyl,
• said reaction occurring in the presence of a base, a palladium catalyst, and a copper catalyst.

A compound of formula 4:

• wherein:
• R1, R2, R3, and R4 each are independently selected from the group consisting of H, halogen, —CN, —CHO, —CF3, —OCF3, —OH, —NO2, —C1-6 alkyl, Con alkoxy, —NH2, —NH(C1-6 alkyl), —N(C1-6 alkyl)2, and —NHC(O)—C1-6 alkyl;
• and
• R5 is selected from the group consisting of H and —C(O)O—C1-6 alkyl.