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. Author manuscript; available in PMC: 2014 Jun 3.
Published in final edited form as: Angew Chem Int Ed Engl. 2013 Apr 24;52(23):6043–6046. doi: 10.1002/anie.201300135

Table 3.

Copper-Catalyzed Amination of 8-Amino-quinoline Amides[a]

graphic file with name nihms-497618-t0016.jpg

entry amine product yield, %
1 HNMeBn graphic file with name nihms-497618-t0017.jpg 82
2 HNMePr graphic file with name nihms-497618-t0018.jpg 74
3 4-EtO2C-
piperidine
graphic file with name nihms-497618-t0019.jpg 69
4 4-NC-
piperidine
graphic file with name nihms-497618-t0020.jpg 71
5 Ethylene ketal
of 4-keto-
piperidine
graphic file with name nihms-497618-t0021.jpg 82
6 4-BocNH-
piperidine
graphic file with name nihms-497618-t0022.jpg 83
7 Cyclohexyl-
amine
graphic file with name nihms-497618-t0023.jpg 40
8 Cyclooctyl-
amine
graphic file with name nihms-497618-t0024.jpg 52
9 Neopentyl-
amine
graphic file with name nihms-497618-t0025.jpg 32
10[b] n-C12H25NH2 graphic file with name nihms-497618-t0026.jpg 20
[a]

Scale: 0.5 mmol, 2 mL NMP, 2 equiv NMO, 2 equiv amine, 12-25 mol% Cu(OAc)2, 12-25 mol% Ag2CO3, 110 °C, 12 h. Yields are isolated yields.

[b]

Pyridine solvent. Please see Supporting Information for details.