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. 2016 Aug 9;7(10):884–889. doi: 10.1021/acsmedchemlett.6b00188

Scheme 2. General Synthesis of sPLA2 Inhibitors 4 and 7–9.

Scheme 2

Conditions: (a) appropriate malonate, Cs2CO3, DMF, 70 °C, 2 h. (b) NaOH (4 equiv), H2O/MeOH 3:1 80 °C 2 h. (c) HOAc (3 M), reflux. (d) HCl, MeOH 60 °C, 2.5 h. (e) (Bpin)2 (1.3 equiv), KOAc (2.5 equiv), PdCl2(dppf) (6.5 mol %), dioxane, 90 °C. (f) BnZnBr (1.5 equiv, 0.5 M in THF), Pd(PPh3)4 (5 mol %), THF, 60 °C, 2 h. (g) Compound 4: 3-(3-methoxy-3-oxopropyl)phenylboronic acid (commercial), Pd(Ph3)4. Compound 7: PdCl2(dbpf) (5 mol %), C. Cs2CO3, DMF, 90 °C, 1.5 h. (h) n-Propanol/H2O (10:1), KOH (10 equiv), 80–100 °C. (i) B, PdCl2(dppf), Cs2CO3, DMF, 90 °C.