Sodium triacetoxyborohydride → 6-(2-{4-[2-(4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}ethyl)pyridine-3-carbonitrile

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Reaction Steps

A mixture of 6-[2-(2-Oxopiperazin-1-yl)ethyl]pyridine-3-carbonitrile [I-14](1 eq), (4-Methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (1 eq) and NaBH(OAc)3 in 10 mL of DCM was stirred overnight at RT. The mixture was diluted with 50 mL of DCM and washed with brine, concentrated and the residue was purified by prep-TLC (DCM:MeOH=15:1) to afford the title product. 1H-NMR (400 MHz, CDCl3) δ ppm 8.73 (s, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 5.18 (s, 2H), 3.71 (t, J=7.2 Hz, 2H), 3.26 (s, 2H), 3.08-3.14 (m, 4H), 2.85 (t, J=7.6 Hz, 2H), 2.65 (s, 2H), 2.54 (t, J=7.6 Hz, 2H), 2.21 (s, 3H).

Provenance & Evidence