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. Author manuscript; available in PMC: 2022 Dec 23.
Published in final edited form as: J Med Chem. 2021 Dec 2;64(24):18054–18081. doi: 10.1021/acs.jmedchem.1c01476

Scheme 3. Synthesis of GDC-0068-Based CRBN-Recruiting Compounds 14–25 (A), 26 (B), 27 (C), and 28 and 29 (D)a.

Scheme 3.

aReaction conditions: (a) EDCI, HOAt, NMM, DMSO, rt, 12 h; (b) TFA/DCM, rt, 30 min; (c) 4-toluenesulfonyl chloride, NEt3, DCM, 0 °C to rt, 4 h; (d) NaCN, NaI, DMF, 50 °C, 8 h; (e) 4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione, Pd(PPh3)2Cl2, CuI, NEt3, DMF, 70 °C, 2 h; (f) Raney Ni, H2, MeOH/NH3.H2O (3/1), rt, 1 h; and (g) NaHCO3, KI, DMF, 60 °C, overnight.