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. Author manuscript; available in PMC: 2018 Sep 23.
Published in final edited form as: ChemMedChem. 2016 Oct 5;11(21):2410–2421. doi: 10.1002/cmdc.201600417

Scheme 4.

Scheme 4

Synthesis of erlotinib prodrugs 2a and 2c. Reagents and conditions: a) 4-nitrobenzyl bromide, tBuOK, DMF abs.; b) Boc-4-aminobenzyl bromide, tBuOK, DMF abs.; c) HCl conc., MeOH; d) 9, HOBt·H2O, DMF abs.