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. 2018 Dec 12;62(2):699–726. doi: 10.1021/acs.jmedchem.8b01413

Scheme 1. Synthesis of the BRD7/9 Ligand 1c.

Scheme 1

Reagents and conditions: (a) 1-Boc-piperazine, NaBH(OAc)3, THF, rt, overnight, yield 97%; (b) NaH, CH3I, DMF, 0 °C, 5 h, yield 95%. (c) Step 1: 12, B2pin2, KOAc, Pd(dppf)Cl2, 1,4 dioxane, microwave, 140 °C, 40 min. Step 2: 14 and K2CO3 (aq) are added to step 1; microwave, 120 °C, 30 min, yield 55%. (d) HCl 4 M in dioxane, DCM, rt, 1 h, quantitative yield.