Processes and intermediates for preparing mcl1 inhibitors

A compound selected from:

• wherein
• X is halogen,
• C(O)2R1, —OS(O)2R2, or —OP(O)(R2)2, wherein R1 is H or C1-6alkyl, each R2 is C1-6alkyl or C6-10aryl, each R7 is independently H or C1-3alkyl, wherein each alkyl or aryl is optionally substituted with one to four halogen or C1-3alky, m is 1, 2, or 3, and n is 0 or 1;
• and
• R4 is halogen, and Rc is C1-6alkyl.

A method of preparing a compound 1:

• or a salt thereof, comprising preparing a compound of formula 9-A:
• by reacting a corresponding compound of formula 1-K:
• with a corresponding compound of formula 6-L:
• to provide the compound of formula 9-A or the salt thereof, wherein the compound of formula 1-K is prepared by converting a corresponding compound of formula 1-Q:
• to the compound of formula 1-K or salt thereof,
• wherein Rx and Ry are each independently H or C1-6alkyl;
• R2 is H;
• R3 and R5 are each independently CH3;
• Rz is halogen or CN;
• and Rp is selected from —C(═O)—C1-6alkyl, —C(═O)—C6-10aryl, —C(═O)—O—C1-6alkyl, —C(═O)—O—C1-6alkyl-C6-10aryl, and —C(═O)—O—C6-10aryl, wherein each aryl is optionally substituted with one to four groups independently selected from C1-3alkyl and —OC1-3alkyl.