Process for the preparation of indolin-2-one derivatives useful as PR modulators

Processes for dialkylating indolinones, specifically indolin-2-ones are provided. The processes for dialkylating an indolin-2-one include performing the dialkylation in the presence of at least 2 equivalents of a first base, a second base containing at least 1 equivalent of lithium diisopropylamide, and an alkylating agent. Processes for preparing a compound of the structure are provided, wherein R1, R3, R4, R6, R7, R9, and R10 are as defined herein. In one embodiment, a process for preparing 5-(4'-fluoro-2'-oxospiro[cyclopropane-1,3'-indoline]-5'-yl)-1-methyl-1H-pyrrole-2-carbonitrile is provided.