Water → HCID 53259467, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (41 mg, 0.14 mmol) and TBAI (2.6 mg, 6.9 μmol) in THF (0.6 ml) was added sodium hydride (7.0 mg, 95%, 2.8 mmol) at 0° C. The yellow suspension was stirred for 20 min at 0° C. under argon. A solution of 5-(2-(bromomethyl)phenyl)-3-methyl-1,2,4-oxadiazole in dry THF (0.4 ml) was added and stirring was continued for 2 h at rt. To the reaction mixture was added water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over sodium sulfate, filtered and evaporated to give 64 mg (98%) of a pale brown oil. [1H NMR (600 MHz, DMSO-d6) ♀ ppm 8.84 (s, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.81 (d, J=8.3 Hz, 1H), 7.68 (t, J=7.7 Hz, 1H), 7.55-7.62 (m, 2H), 7.51 (t, J=7.8 Hz, 1H), 7.34-7.41 (m, 1H), 7.27 (d, J=7.7 Hz, 1H), 4.91 (s, 2H), 4.23-4.34 (m, 2H), 3.46 (t, J=11.1 Hz, 2H), 3.26-3.32 (m, 2H), 2.44 (s, 3H), 2.04-2.12 (m, 2H), 1.93-2.01 (m, 2H), 1.83-1.92 (m, 2H), 1.66 (d, J=13.5 Hz, 2H); LCMS RtD=2.63 min, [M+H]+=469.2].

Provenance & Evidence