(m, 1H), six.ten (d, J = 6.2 Hz, 1H), five.69 (m, 1H), five.33 (m, 1H), 4.19-4.35 (m, 2H), two.43 (s, 3H), 1.31 (m, 3H). 13C NMR (one hundred MHz): 144.9, 138.5, 132.7, 129.4, 128.9, 128.three, 128.1, 126.0, 123.8, 123.three, 120.7, 120.four, 104.4, 104.1, 78.3, 66.9, 63.0, 50.0, 49.four, 34.1, 21.6, 14.three. Anal. Calcd for C23H21ClN2O4S: C, 60.46; H, 4.63; N, 6.13. Discovered: C, 60.64; H, four.46; N, 5.96. N-Ethoxycarbonyl-1,2-dihydro-2-(N-phenyl-N-tosylaminoethynyl)-4-bromopyridine, 13. The ynamide (54.2 mg, 0.20 mmol), CuI (3.eight mg, 0.02 mmol) and N,N-diisopropylethylamine (70 L, 0.40 mmol) have been dissolved in 1 mL of anhydrous acetonitrile. Then, a answer of 4-bromopyridine hydrochloride (46.7 mg, 0.24 mmol), N,N-diisopropylethylamine (70 L, 0.40 mmol), and ethyl chloroformate (38 L, 0.40 mmol) in two mL of anhydrous acetonitrile was added. The reaction was completed just after 20 h. Chromatographic purification (1:four EtOAc/hexanes) gave 72.4 mg (0.14 mmol, 72 ) of a slightly yellow oil. 1H NMR (400 MHz): 7.47-7.61 (m, 2H), 7.23-7.36 (m, 5H), 7.14-7.22 (m, 2H), six.82 (m, 1H), 5.71 (m, 1H), five.57 (d, J = six.eight Hz, 1H), 5.31 (dd, J = eight.0, 2.1 Hz, 1H), four.20-4.34 (m, 2H), two.44 (s, 3H), 1.30 (s, 3H). 13C NMR (100 MHz): 144.9, 138.4, 132.five, 129.4, 129.0, 128.four, 128.2, 127.1, 126.6, 126.0, 113.eight, 113.three, 106.six, 78.4, 68.2, 63.0, 45.five, 45.1, 21.7, 14.3. Anal. Calcd for C23H21BrN2O4S: C, 55.ten; H, 4.22; N, five.59. Located: C, 54.73; H, four.63; N, 5.28. N-Ethoxycarbonyl-1,2-dihydro-2-(N-phenyl-N-tosylaminoethynyl)-4-phenylpyridine, 14. The reaction in between the ynamide (54.2 mg, 0.20 mmol) and 4-phenylpyridine (37.2 mg, 0.24 mmol) was completed immediately after 2.five h. Chromatographic purification (1:4 EtOAc/hexanes) gave 95.5 mg (0.19 mmol, 96 ) of a slightly yellow oil. 1H NMR (400 MHz): 7.46-7.58 (m, 2H), 7.23-7.46 (m, 8H), 7.16-7.23 (m, 2H), 7.02-7.16 (m, 2H), six.RuPhos Pd G2 Formula 92 (m, 1H), 5.2-Cyclopentenone manufacturer 69-5.PMID:24635174 91 (m, 3H), 4.22-4.37 (m, 2H), 2.36 (s, 3H), 1.27-1.40 (m, 3H). 13C NMR (one hundred MHz): 153.six, 152.eight, 144.eight, 144.7, 138.six, 138.three, 134.6, 134.3, 132.six, 129.three, 128.9, 128.six, 128.four, 128.2, 128.1, 128.0, 126.0, 125.8, 125.five, 113.9, 113.4, 106.two, 77.7, 69.1, 62.7, 44.five, 44.0, 21.6, 14.5. Anal. Calcd for C29H26N2O4S: C, 69.86; H, five.26; N, 5.62. Discovered: C, 69.76; H, five.47; N, 5.56. N-Ethoxycarbonyl-2-(N-phenyl-N-tosylaminoethynyl)-2,3-dihydro-4-pyridone, 15. The reaction in between the ynamide (54.two mg, 0.20 mmol) and 4-methoxypyridine (25 L, 0.24 mmol) was completed just after 2.five h. Acidic workup (1 M aqueous HCl) followed by chromatographic purification (1:1 EtOAc/hexanes, Al2O3) gave 68.2 mg (0.16 mmol, 78 ) of a slightly yellow oil. 1H NMR (400 MHz): 7.75 (d, J = 8.4 Hz, 1H), 7.47 (d, J = eight.three Hz, 2H), 7.22- 7.34 (m, 5H), 7.08-7.18 (m, 2H), five.51 (d, J = 6.three Hz, 1H), five.43 (dd, J = eight.four, 1.3 Hz, 1H), 4.27-4.41 (m, 2H), two.88 (dd, J = 16.3, six.5 Hz, 1H), two.59 (ddd, J = 16.3, 1.6, 1.six Hz, 1H), 2.44 (s, 3H), 1.35 (t, J = 7.1 Hz, 3H). 13C NMR (100 MHz): 191.three, 152.1, 145.two, 141.3, 138.two, 132.five, 129.6, 129.1, 128.3, 128.2, 126.0, 107.five, 77.9, 66.9, 63.9, 45.5, 41.six, 21.7, 14.3. Anal. Calcd for C23H22N2O5S: C, 63.00; H, five.06; N, 6.39. Discovered: C, 62.74; H, four.99; N, six.09. N-Ethoxycarbonyl-1,2-dihydro-2-(N-phenyl-N-tosylaminoethynyl)quinoline, 16. The reaction amongst the ynamide (54.2 mg, 0.20 mmol) and quinoline (29 L, 0.24 mmol) was completed after 2.5 h. Chromatographic purification (three:8 Et2O/hexanes) gave 86.0 mg (0.18 mmol, 91 ) of a slightly yellow oil. 1H NMR (400 MHz): 7.59 (d, J = 8.3 Hz, 1H), 7.11-7.30 (m, 8H), 7.06-7.11 (m, 2H), 6.93-7.00 (m, 2H),.