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. Author manuscript; available in PMC: 2012 Jan 21.
Published in final edited form as: ChemMedChem. 2009 Oct;4(10):1615–1629. doi: 10.1002/cmdc.200900226

Scheme 2.

Scheme 2

Reagents and conditions: a) K2CO3, methyl ethyl ketone, 3-bromo-2-methylpropene; b) K2CO3, [Pd(OAc)2], nBu4NCl, DMF, PhB(OH)2 for 11 b or 1-penten-1-ylboronic acid for 11 c; c) NaOH, EtOH, THF, H2O; d) HATU, DiPEA, DMF, CH2Cl2, 2-iodoaniline for 16 or cyclohexylamine for 17 and 20 or piperidine for 18 and 19 or neopentylamine for 21 or morpholine for 22 or N-tert-butylmethylamine for 23 or 4-(aminomethyl)tetrahydropyran for 24.