2-Amino-4-bromobenzonitrile → tert-Butyl 4-(3-amino-4-cyanophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Steps

Following the same procedure adopted for the synthesis of 22, the reaction of nitrile 11 with boronic ester 21 afforded the title compound 24 as an off-white solid (62%). IR (KBr) νmax. cm−1: 3421, 3318 (NH2), 3072 (Ar—H), 2247 (CN), 1691 (C═O), 1616, 1510, 1412 (C═C). 1H-NMR (500 MHz, CDCl3) δ=1.49 (s, 9H, (CH3)3C); 1.71 (br. s, 2H, CH2); 2.45 (br. s, 2H, CH2); 3.61 (m, 2H, CH2); 4.07 (s, 2H CH2); 4.43 (br. s, 2H, NH2); 6.10 (br. s, 1H, CH); 6.71 (d, J=2.2 Hz, 1H, H-2); 6.75 (dd, 1H, J=2.3, 8.6 Hz, H-6); 7.33 (d, J=8.5 Hz, 1H, H-5); 8.01 (br. s, 1H, NH); 13C NMR (125.7 MHz, CDCl3) δ=27.35 (CH2), 28.47 (CH3)3C), 29.73 (CH2), 41.96 (CH2), 79.91 (CH3)3C), 94.63 (aromatic-C), 115.12 (aromatic-C), 117.69 (CN), 133.67 (aromatic-C), 147.42 (aromatic-C), 150.47 (aromatic-C), 155.33 (C═O). Calculated (%) for C17H21N3O2 (299.16); C, 68.20; H, 7.07; N, 14.04. found (%; C, 68.16; H, 7.13; N, 13.97.

Provenance & Evidence