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. Author manuscript; available in PMC: 2020 Dec 11.
Published in final edited form as: J Med Chem. 2020 Apr 14;63(8):4293–4305. doi: 10.1021/acs.jmedchem.0c00200

Scheme 3.

Scheme 3.

Reagents and conditions: (a) urotropine, chloroform, 50°C then EtOH, HCl(aq), rf (97%); (b) KSCN, HOAc, rf (71%); (c) 2-bromoethan-1-ol, K2CO3, MeOH, rt (quant.); (d) NaH, SEM-Cl, THF, 0°C (67%); (e) NBS, MeCN, −30°C (quant.);(f) NaH, MeI,THF, −15°C (75%); (g) N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide, P(t-bu)3 Pd G3, K3PO4, 1,4-dioxane/water, 50°C (56%%); (h) NaOH, THF/water, 50°C (59%); (i) N-(3-bromo-4-methoxyphenyl)acrylamide, Brettphos Pd G3, Cs2CO3, t-BuOH/1,4-dioxane, rf (44%); (j) HCl in EtOH 2.5 M, rt (70%).