One-Pot Approach to N-Quinolyl 3′/4′-Biaryl Carboxamides by Microwave-Assisted Suzuki–Miyaura Coupling and N-Boc Deprotection

Abstract

N-Quinolyl biaryl carboxamides have received tremendous attention for their notable biological properties. Here we have described a general protocol for the preparation of N-quinolyl 3'/4'-biaryl carboxamides by microwave-assisted Suzuki-Miyaura cross-coupling reaction and N-Boc deprotection in one pot. This method, which did not require acids, was used to produce a series of N-quinolyl 3'/4'-biaryl carboxamides with excellent functional group tolerance and high yields (70% to 95%).

Cobalt-Catalyzed Carbonylative Synthesis of Phthalimides from N-(Pyridin-2-ylmethyl)benzamides with TFBen as the CO Source

“…The multiplicities of the signals were reported as s (singlet), d (doublet), t (triplet), dd (doublet of doublets), or m (multiplet), and coupling constants (J) were given in hertz. 13 C NMR spectra were obtained at 101 MHz, and they were calibrated with CDCl 3 (δ = 77.0 ppm) or DMSO (δ = 39.5 ppm).…”

“…1 H NMR (400 MHz, CDCl 3 ): δ 8.24 (s, 3H), 6.97 (s, 3H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ): δ 158. 1, 150.3, 112.6.…”

“…1 H NMR (400 MHz, CDCl 3 ): δ 8.51 (d, J = 4.7 Hz, 1H), 7.85 (s, 1H), 7.80 (d, J = 8.1 Hz, 2H), 7.63 (td, J = 7.7, 1.5 Hz, 1H), 7.29 (d,J = 7.8 Hz,1H),7.22 (d,J = 8.0 Hz,2H),1H), 4.72 (d, J = 5.0 Hz, 2H), 2.66 (q, J = 7.6 Hz, 2H), 1.23 (t, J = 7.6 Hz, 3H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ): δ 167. 3, 156.6, 148.8, 147.9, 136.6, 131.6, 127.8, 127.1, 122.1, 121.9, 44.6, 28.6, 15. .18 (dd, J = 6.9, 5.3 Hz, 1H), 4.74 (d, J = 5.0 Hz, 2H), 1.32 (s, 9H).…”

“…3, 156.6, 148.8, 147.9, 136.6, 131.6, 127.8, 127.1, 122.1, 121.9, 44.6, 28.6, 15. .18 (dd, J = 6.9, 5.3 Hz, 1H), 4.74 (d, J = 5.0 Hz, 2H), 1.32 (s, 9H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ): δ 167. 3, 156.5, 154.8, 148.8, 136.6, 131.4, 126.9, 125.3, 122.2, 122.0, 44.7, 34.8, 31.1. 4-Methoxy-N-(pyridin-2-ylmethyl)benzamide, 1e.…”

Eco-Friendly Physical Activation Methods for Suzuki–Miyaura Reactions

“…An efficient synthesis of N-quinoline 3′/4′-biaryl carboxamides, which avoids the protection/deprotection of the amide function, has recently been described as being based around a one-pot, MW-assisted SMC and N-Boc-deprotection sequence [59]. The mixture with 2.0 mol % of Pd(PPh3)4, phenylboronic acid (1 equiv.)…”