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. 2018 Oct 23;9(12):2055–2067. doi: 10.1039/c8md00448j

Scheme 1. Reagents and conditions: (i) 4-(2-Chloroethyl)morpholine hydrochloride, methyl 5-bromovalerate, or methyl 4-bromomethylbenzoate, Cs2CO3, DMF, 50 °C, 12 h, 22–37%; (ii) 4-methoxyphenylboronic acid, Pd(OAc)2, Na2CO3, H2O : DMF 1 : 4 v:v, 110 °C, 3 h, 55%; (iii) 10% aq. NaOH, EtOH, 110 °C, 5 h, 43%; (iv) N-Boc-1,8-octanediamine or N-Boc-2,2′-(ethylenedioxy)diethylamine, DIPEA, HATU, DMF, rt, 14 h, 71–77%; (v) TFA, DCM, rt, 1 h, 86–91%; (vi) Ac2O, DIPEA, DCM, rt, 1 h, 95–96%; (vii) BODIPY 630/650-X-OSu, DIPEA, DMF, rt, 15 h, 88–92%. Compounds 1 : 1 cis/trans.

Scheme 1