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. 2021 Jul 27;64(15):11614–11636. doi: 10.1021/acs.jmedchem.1c00957

Scheme 1. Synthesis Pathway Used in R1 and Hydroxymethyl Group Position Optimization of m-Terphenyls 4a–4h.

Scheme 1

Reagents and conditions: (a) 1a–c, 4-benzodioxane-6-boronic acid, Pd(dppf)Cl2·DCM, K2CO3, dioxane/water 2:1, 80 °C, 3 h, 47–61%; (b) 2a–c, (hydroxymethyl)phenylboronic acid, Pd(dppf)Cl2·DCM, K2CO3, dioxane/water 2:1, 80 °C, 3 h, 32–56%; (c) for 4f: 4d (R1 = NH2), HBr, NaNO2, CuBr2, 70 °C, 2 h, 9%; for 4g: 4d (R1 = NH2), HCl, NaNO2, KI, RT, 16 h, 28%; for 4h: 4d (R1 = NH2), HCl, NaNO2, CuCN, KCN, RT, 4 h, 21%.