Skip to main content
. 2022 Dec 16;66(1):306–332. doi: 10.1021/acs.jmedchem.2c01256

Scheme 3. Reagents and Conditions.

Scheme 3

(a) Appropriate aryl bromide, Pd(PPh3)4, tetrabutyl ammonium bromide (TBAB), EtOH/2 Maq Na2CO3, 1,2-dimethoxyethane or EtOH/toluene, reflux; (b) 2-chloro-N,N-diethylethylamine hydrochloride, K2CO3, KI, methyl ethyl ketone, reflux; (c) iodoethane: neat, reflux for 8, 9, 25, 26; DCM, rt for 27; THF, reflux for 30–32; (d) Ac2O, H2SO4, 80 °C; (e) 1° step: ClCOCOCl, DCM, DMF, rt; 2° step: aniline, DCM, rt; (f) 1 M NaOH, MeOH, rt; (g) 1-chloro-2-bromoethane, Cs2CO3, DMF, 60 °C; (h) NaI, acetone, reflux; (i) diethylamine, reflux; (j) benzoic anhydride, sodium octyl sulfate, H2O, CH3CN, rt; (k) 1° step: aniline, NaNO2, 37% HCl, H2O, 0 °C to rt; 2° step: NaHCO3, rt; (l) KOH, MeOH, reflux; (m) tert-butyl (S)-3-hydroxypyrrolidine-1-carboxylate, PPh3, diisopropyl azodicarboxylate (DIAD), THF, −10 °C to reflux; (n) LiAlH4, THF, −10 °C to reflux; and (o) iodomethane, THF, 40 °C.