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. 2021 Feb 26;118(9):e2021102118. doi: 10.1073/pnas.2021102118

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Copyright © 2021 the Author(s). Published by PNAS.

This open access article is distributed under Creative Commons Attribution License 4.0 (CC BY).

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Scheme 1. — Syntheses of DEC-Tec selection hits 3 to 12. Reagents and conditions: step a, 4-(methylcarbamoyl)benzoic acid, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), N,N-diisopropylethylamine (DIEA), N,N-dimethylformamide (DMF), room temperature (rt), 16 h; step b, Zn, AcOH, CH₃OH, rt, 1 h; step c, 3-iodo-1-methyl-1H-indazole-5-carboxylic acid, HATU, DIEA, DMF, rt, 16 h, 27% for 2a and 35% for 2b (three steps); step d, boronic acid derivative, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (Pd(dppf)Cl₂·CH₂Cl₂) (10 mol %), 1,2-dimethoxyethane (DME)/Na₂CO_3(sat) (vol/vol, 1:1), microwave 85 to 110 °C, 1 h; 24 to 94%.