Synthesis of polyaryl substituted aryl compounds

A process for the synthesis of a compound of Formula (1):

• wherein:
• n is 2, 3, or 4;
• each R1 is independently —(CH2)mC(O)ORa or —C(O)ORa;
• each Ra is independently C1-4 alkyl;
• and
• m is 1, 2, 3, 4, 5, 6, 7, or 8;
• wherein the process comprises the following steps:
• (i) reacting a compound of Formula (2):
• wherein:
• n is 2, 3, or 4;
• and
• X is a halogen;
• with a compound of Formula (3):
• wherein:
• Y is —BF3−K+;
• in the presence of a base, an organic solvent optionally comprising water, and a palladium catalyst selected from the group consisting of Pd, PdCl2, Pd(OAc)2, Pd(PPh3)4, PdCl2(PPh3)2, Pd(dba)2, (dppf)PdCl2, Pd2(dba)3, Pd2(dba)3.CHCl3, [PdCl(allyl)]2, [PdCl2(cod)], and a Pd-containing amino acid, under an inert atmosphere, to produce a compound of Formula (4):
• wherein:
• n is 2, 3, or 4;
• and
• (ii) reacting the compound of Formula (4) above with two, three, or four compounds of Formula (5):
• wherein:
• each D is independently a halogen;
• each R1 is independently —(CH2)mC(O)ORa or —C(O)ORa;
• each Ra is independently C1-4 alkyl;
• and
• m is 1, 2, 3, 4, 5, 6, 7, or 8;
• in the presence of a base, dry solvent, and a palladium catalyst selected from the group consisting of Pd, PdCl2, Pd(OAc)2, Pd(PPh3)4, PdCl2(PPh3)2, Pd(dba)2, (dppf)PdCl2, Pd2(dba)3, Pd2(dba)3.CHCl3, [PdCl(allyl)]2, [PdCl2(cod)], and a Pd-containing amino acid, under an inert atmosphere, to produce the compound of Formula (1) above.