(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine → 5-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]-2-methoxy-N,N-dimethylnicotinamide

Participants

Reaction Steps

The title compound was synthesized as described for Intermediate I-28 in 38% yield starting from (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman -3-amine and 5-bromo-2-methoxy-N,N-dimethylnicotinamide. The reaction mixture was irradiated in a microwave at 140° C. for 45 min: 1H NMR (400 MHz, DMSO-d6) ppm 8.19 (d, 1 H), 7.68 (d, 1 H), 7.25-7.40 (m, 8 H), 7.11-7.22 (m, 3 H), 6.70-6.80 (m, 2 H), 4.32-4.38 (m, 1 H), 3.97-4.04 (m, 1 H), 3.96 (s, 3 H), 3.62-3.75 (m, 4 H), 3.02-3.13 (m, 2 H), 2.99 (s, 3 H), 2.91-2.98 (m, 1 H), 2.85 (s, 3 H); MS (ESI) m/z 508[M+H+].

Provenance & Evidence