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. 2023 Feb 2;66(4):2832–2850. doi: 10.1021/acs.jmedchem.2c01884

Scheme 2. Synthesis of HSD17B13 Chemical Probe 45 (BI-3231).

Scheme 2

Reagents and conditions: (a) MeSO2Cl, NEt3, CH2Cl2, 90% yield; (b) N,O-bis(trimethylsilyl)acetamide, MeCN, 76% yield; (c) EtI, K2CO3, DMF, 69% yield; (d) [bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride, EtOH, water, 51% yield; (e) 1-(chloromethyl)-4-methoxybenzene, K2CO3, MeCN, quant. yield; (f) n-BuLi, tetrahydrofuran (THF), −78 °C, trimethyl borate, then 4 M HCl, 91% yield; (g) trifluoroacetic acid (TFA), CH2Cl2, 69% yield.