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. Author manuscript; available in PMC: 2018 Jan 1.
Published in final edited form as: J Heterocycl Chem. 2015 Nov 25;54(1):155–160. doi: 10.1002/jhet.2559

Table 2.

Preparation of 7-Aryl Derivatives of Tirapazamine.

graphic file with name nihms-741301-f0006.jpg
Aryl halide R2, product Yield [%] Ligand Base Solvent
4a 4-methoxyphenyl, 11 46 SPhos Cs2CO3 Toluene
4b 72 SPhos Cs2CO3 Toluene
4b 4-aminophenyl, 12 30 PCy3 K3PO4 Toluene/Water
4b 4-cyanophenyl, 13 60 SPhos Cs2CO3 Toluene
4b 2-Naphtyl-6'-methoxy, 14 27 PCy3 K3PO4 Toluene/Water