Efficient Electrochemical N-Alkylation of N-Boc-Protected 4-Aminopyridines: Towards New Biologically Active Compounds

Table 1

Alkylation reaction of 𝑁-Boc-4AP using electrogenerated acetonitrile anion in MeCN-0.1 M TEAHFP, followed by deprotection with trifluoroacetic acid^a.

Entry	R–X	1, yield	2, yield
1
2
3
4
5
6
7
8
9
10

aThe reduction was conducted under galvanostatic conditions (20 mA cm⁻²), on Pt electrodes in a divided cell at rt, on 20 mL MeCN-0.1 M TEAHFP solution containing 1 mmol of 4AP. At the end of the electrolysis, 1 mmol of alkylating agent was added. After 2 h at rt, usual workup afforded the products. Deprotection was carried out as described in the experimental part. All the yields are in isolated products. ^bWhen compounds 2g–i were subjected to deprotection with trifluoroacetic acid, a large amount of 4AP was obtained.