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. 2021 Nov 30;64(23):17079–17097. doi: 10.1021/acs.jmedchem.1c00946

Scheme 2. Synthesis of Quinolinone Compounds Shown in Tables 1–4.

Scheme 2

Reagents and conditions: a) 12M HCl, 1,4-dioxane, reflux, 18 h; b) H2SO4, HNO3, 0 °C, 1 h; c) requisite amine, NMP, 160 °C, up to 16 h; d) requisite boronate ester, Pd(PPh3)4, 2M aq Na2CO3 140 °C, 1 h; e) SnCl2, ethanol, trifluoroethanol, 120 °C, 1 h; f) Pd/C (10% w/w), ammonium formate, ethanol or NMP, 60 °C, up to 4h; g) 2,4-dichloropyridine-3-carbonitrile, Et3N or DIPEA, 160 °C, 1 h; h) NaH (60% in mineral oil, DMF, MeI, rt, 90 min; i) requisite amine, Pd(OAc)2, Cs2CO3, rac-BINAP, PhMe, 120 °C, <4 h; j) 4,6-dichloro-5-cyano-pyridine-2-carboxylic acid, NMP, 100 °C, 2 h; k) Cs2CO3, bromomethylcyclopropane or bromomethylcyclobutane, DMF, rt, 1−2 d.