N-丙基-4-溴苯甲酰胺

反应条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of N-n-propyl-4-bromobenzamide from Example 9A, phenylacetylene (1.5 eq.) and Pd(PPh3)2Cl2 (5 mol %) in piperidine (3 eq.) was heated at 70° C. for 30 minutes in a sealed tube. The solidified residue was dissolved with CH2Cl2 and water and poured onto HCl 2N. The acidic phase was extracted three times with CH2Cl2. The combined organic layers were washed once with HCl 2N, twice with saturated NaHCO3, once with water and once with brine. The organic layer was then dried over MgSO4 and concentrated. The resulting residue was purified using SiO2 with CH2Cl2/petroleum ether 80:20 to CH2Cl2 100% to give N-n-propyl-3-phenylethynyl-benzamide as a yellow solid (Quantitative yield). NMR 1H (ppm, CDCl3): 7.73 (d. J3=8.4 Hz, 2H), 7.63-7.51 (m, 5H), 7.36-7.32 (m, 2H), 6.10 (br. s., 1H), 3.45-3.37 (m, 2H), 1.64 (sext., J=7.2 Hz, 2H), 0.99 (t, J3=7.4 Hz, 3H). poured onto HCl 2N The acidic phase was extracted three times with CH2Cl2 The combined organic layers were washed once with HCl 2N, twice with saturated NaHCO3, once with water and once with brine The organic layer was then dried over MgSO4 concentrated The resulting residue was purified

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Using Preparation Method 2, N-n-propyl-4-bromobenzamide from Example 9A was reacted with phenylboronic acid. The resulting reaction mixture was purified using SiO2 with CH2Cl2/Petroleum Ether 80:20 to CH2Cl2/AcOH 80:20 to give a white solid (71%). NMR 1H (ppm, CDCl3): 7.82 (d, J3=8.32 Hz, 2H), 7.63 (d, J3=8.69 Hz, 2H), 7.59 (d, J3=7.14 Hz, 2H), 7.45 (t, J3=7.09 Hz, 2H), 7.39-7.34 (m, 1H), 6.14 (br. s., 1H), 3.47-3.41 (m, 2H), 1.65 (sext., J3=7.18 Hz, 2H), 0.99 (t, J3=7.37 Hz, 3H). The resulting reaction mixture was purified

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Using Preparation Method 2, N-n-propyl-4-bromobenzamide from Example 9A was reacted with phenylboronic acid. The resulting reaction mixture was purified using SiO2 with CH2Cl2/Petroleum Ether 80:20 to CH2Cl2/AcOH 80:20 to give a white solid (71%). NMR 1H (ppm, CDCl3): 7.82 (d, J3=8.32 Hz, 2H), 7.63 (d, J3=8.69 Hz, 2H), 7.59 (d, J3=7.14 Hz, 2H), 7.45 (t, J3=7.09 Hz, 2H), 7.39-7.34 (m, 1H), 6.14 (br. s., 1H), 3.47-3.41 (m, 2H), 1.65 (sext., J3=7.18 Hz, 2H), 0.99 (t, J3=7.37 Hz, 3H). The resulting reaction mixture was purified

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Using Preparation Method 1, 4-bromobenzoic acid was reacted with n-propylamine. The resulting reaction mixture was purified using SiO2 With 100% CH2Cl2 to give a white solid (67%). NMR1H (ppm, CDCl3): 7.61 (d, J3=8.60 Hz, 2H), 7.54 (d, J3=8.57 Hz, 2H), 6.06 (br. s., 1H), 3.43-3.37 (m, 2H), 1.62 (sext., J3=7.25 Hz, 2H), 0.97 (t, J3=7.39 Hz, 3H). The resulting reaction mixture was purified