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. Author manuscript; available in PMC: 2011 Jun 21.
Published in final edited form as: Org Biomol Chem. 2010 May 6;8(12):2719–2727. doi: 10.1039/c001036g

Scheme 2.

Scheme 2

Synthesis of azido-BODIPY probes 14 and 16. Reagents and conditions: (i) Hydrazine monohydrate (60 equiv.), MeOH, reflux, 2 h, 88%. (ii) (a) HCl (2.8 equiv.), tBuONO (1.1 equiv.), DMF–EtOAc (1: 1, v/v), −25 °C, 4 h. (b) TFA·H-LeuVS (1.1 equiv.), DiPEA (3.8 equiv.), −25 °C to RT, 15 h, 75%. (iii) TFA/DCM 1: 1 (v/v), 30 min. (iv) 13 (1 equiv.), DiPEA (1 equiv.), DCM, 15 h, 14 54%, 16 27%. (v) (a) HCl (2.8 equiv.), tBuONO (1.1 equiv.), DMF–EtOAc (1: 1, v/v), −25 °C, 4 h. (b) TFA·H-LeuEK (1.1 equiv.), DiPEA (3.8 equiv.), −25 °C to RT, 15 h, 71%.