(E)-3-(3-胺苯基)丙烯酸乙酯

反应条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of methyl (E)-3-aminocinnamate (9) (1.20 g, 6.77 mmol), 1-methylpyrrole-2-carboxylic acid (0.89 g, 7.11 mmol) and EDCI.HCl (1.56 g, 8.14 mmol) in pyridine (8 mL) was stirred at 50° C. for 2.5 h and then cooled and diluted with water. The precipitated semi-solid was dissolved in CH2Cl2, the solution was washed with 0.5 N HCl (2×) and water (2×) and then dried and concentrated under reduced pressure below 30° C. The residue was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (10:1), to yield a solid which was triturated with i-Pr2O/petroleum ether to give thermally unstable methyl (E) -3- (l-methylpyrrole-2-carboxamido)cinnamate (10) (1.42 g, 74%), mp 89-90° C. 1H NMR [(CD3)2SO] δ9.83 (s, 1 H, NH), 8.01 (d, J=1.4 Hz, 1 H, H-2), 7.76 (dt, J=7.8, 1.4 Hz, 1 H, H-4), 7.63 (d, J=16.0 Hz, 1 H, PhCH═CH), 7.45-7.35 (m, 2 H, H-5,6), 7.05 (dd, J=4.0, 1.7 Hz, 1 H, H-pyrrole), 7.03 (t, J=2.0 Hz, 1 H, H-pyrrole), 6.54 (d, J=16.0 Hz, 1 H, Ph CH═CH), 6.11 (dd, J=3.8, 2.6 Hz, 1 H, H-pyrrole), 3.89 (s, 3 H, NCH3), 3.74 (s, 3 H, CO2CH3). cooled the solution was washed with 0.5 N HCl (2×) and water (2×) dried concentrated under reduced pressure below 30° C The residue was chromatographed on silica gel eluting with CH2Cl2/EtOAc (10:1) to yield a solid which was triturated with i-Pr2O/petroleum ether

反应条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of methyl (E)-3-aminocinnamate (9) (1.20 g, 6.77 mmol), 1-methylpyrrole-2-carboxylic acid (0.89 g, 7.11 mmol) and EDCI.HCl (1.56 g, 8.14 mmol) in pyridine (8 mL) was stirred at 50° C. for 2.5 h and then cooled and diluted with water. The precipitated semi-solid was dissolved in CH2Cl2, the solution was washed with 0.5 N HCl (2×) and water (2×) and then dried and concentrated under reduced pressure below 30° C. The residue was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (10:1), to yield a solid which was triturated with i-Pr2O/petroleum ether to give thermally unstable methyl (E) -3- (l-methylpyrrole-2-carboxamido)cinnamate (10) (1.42 g, 74%), mp 89-90° C. 1H NMR [(CD3)2SO] δ9.83 (s, 1 H, NH), 8.01 (d, J=1.4 Hz, 1 H, H-2), 7.76 (dt, J=7.8, 1.4 Hz, 1 H, H-4), 7.63 (d, J=16.0 Hz, 1 H, PhCH═CH), 7.45-7.35 (m, 2 H, H-5,6), 7.05 (dd, J=4.0, 1.7 Hz, 1 H, H-pyrrole), 7.03 (t, J=2.0 Hz, 1 H, H-pyrrole), 6.54 (d, J=16.0 Hz, 1 H, Ph CH═CH), 6.11 (dd, J=3.8, 2.6 Hz, 1 H, H-pyrrole), 3.89 (s, 3 H, NCH3), 3.74 (s, 3 H, CO2CH3). cooled the solution was washed with 0.5 N HCl (2×) and water (2×) dried concentrated under reduced pressure below 30° C The residue was chromatographed on silica gel eluting with CH2Cl2/EtOAc (10:1) to yield a solid which was triturated with i-Pr2O/petroleum ether

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

实验步骤: A solution of (E)-methyl 3-(3-nitrophenyl)acrylate (20.14 g, 0.097 mol), Fe (32.5 g, 0.58 mol), concentrated HCl (3.5 ml) in 50% EtOH (100 ml) was refluxed for 2 h. Upon completion, the solution was filtered through Celite and washed with EtOH. The filtrate was concentrated and extracted with dichloromethane. The combined organic phase was dried over MgSO4 and concentrated to afford (E)-methyl 3-(3-aminophenyl)acrylate as a yellow solid (9.73 g, 57%). Upon completion, the solution was filtered through Celite washed with EtOH The filtrate was concentrated extracted with dichloromethane The combined organic phase was dried over MgSO4 concentrated

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

实验步骤: A solution of (E)-methyl 3-(3-nitrophenyl)acrylate (20.14 g, 0.097 mol), Fe (32.5 g, 0.58 mol), concentrated HCl (3.5 ml) in 50% EtOH (100 ml) was refluxed for 2 h. Upon completion, the solution was filtered through Celite and washed with EtOH. The filtrate was concentrated and extracted with dichloromethane. The combined organic phase was dried over MgSO4 and concentrated to afford (E)-methyl 3-(3-aminophenyl)acrylate as a yellow solid (9.73 g, 57%). Upon completion, the solution was filtered through Celite washed with EtOH The filtrate was concentrated extracted with dichloromethane The combined organic phase was dried over MgSO4 concentrated

反应条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of methyl (E)-3-aminocinnamate (9) (1.20 g, 6.77 mmol), 1-methylpyrrole-2-carboxylic acid (0.89 g, 7.11 mmol) and EDCI.HCl (1.56 g, 8.14 mmol) in pyridine (8 mL) was stirred at 50° C. for 2.5 h and then cooled and diluted with water. The precipitated semi-solid was dissolved in CH2Cl2, the solution was washed with 0.5 N HCl (2×) and water (2×) and then dried and concentrated under reduced pressure below 30° C. The residue was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (10:1), to yield a solid which was triturated with i-Pr2O/petroleum ether to give thermally unstable methyl (E) -3- (l-methylpyrrole-2-carboxamido)cinnamate (10) (1.42 g, 74%), mp 89-90° C. 1H NMR [(CD3)2SO] δ9.83 (s, 1 H, NH), 8.01 (d, J=1.4 Hz, 1 H, H-2), 7.76 (dt, J=7.8, 1.4 Hz, 1 H, H-4), 7.63 (d, J=16.0 Hz, 1 H, PhCH═CH), 7.45-7.35 (m, 2 H, H-5,6), 7.05 (dd, J=4.0, 1.7 Hz, 1 H, H-pyrrole), 7.03 (t, J=2.0 Hz, 1 H, H-pyrrole), 6.54 (d, J=16.0 Hz, 1 H, Ph CH═CH), 6.11 (dd, J=3.8, 2.6 Hz, 1 H, H-pyrrole), 3.89 (s, 3 H, NCH3), 3.74 (s, 3 H, CO2CH3). cooled the solution was washed with 0.5 N HCl (2×) and water (2×) dried concentrated under reduced pressure below 30° C The residue was chromatographed on silica gel eluting with CH2Cl2/EtOAc (10:1) to yield a solid which was triturated with i-Pr2O/petroleum ether