1-叠氮基-2-甲氧基乙烷

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

实验步骤: To a solution of 1-bromo-2-methoxyethane (5.00 g, 35.97 mmol) in DMF (25 mL), was added sodium azide (3 equiv.) and the mixture was heated at 50° C. for 48 hours. The reaction mixture was diluted with water (75 mL) and extracted with diethyl ether. The organic extract was dried over MgSO4 and concentrated to furnish 1-azido-2-methoxyethane as a yellow liquid. This azide (200 mg, 1.94 mmol) was added to a solution of 2-Amino-6-ethynylbenzonitrile (250 mg, 1.76 mmol) (Example 267c) in H2O/tert-BuOH=1:2 (15 mL) and the solution was treated consecutively with sodium ascorbate (0.264 mmol) and CuSO4 (0.035 mmol). The reaction mixture was stirred at room temperature for 48 hours, diluted with water and extracted with ethyl acetate. The organic extract was dried over MgSO4 and purified over silica gel (ethyl acetate/hexane 6:4) to furnish the title compound as a white solid in 88% yield. 1H NMR (400 MHz, DMSO-d6) δ 3.26 (s, 3H), 3.78 (t, J=5.2 Hz, 2H), 4.23 (t, J=5.2 Hz, 2H), 6.13 (br s, 2H), 6.80 (dd, J=1.2, 8.4 Hz, 1H), 7.09 (dd, J=1.2, 7.6 Hz, 1H), 7.36 (t, J=8.4 Hz, 1H), 8.52 (s, 1H). MS 244 (MH+). extracted with ethyl acetate The organic extract was dried over MgSO4 purified over silica gel (ethyl acetate/hexane 6:4)

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

实验步骤: To a solution of 1-bromo-2-methoxyethane (5.00 g, 35.97 mmol) in DMF (25 mL), was added sodium azide (3 equiv.) and the mixture was heated at 50° C. for 48 hours. The reaction mixture was diluted with water (75 mL) and extracted with diethyl ether. The organic extract was dried over MgSO4 and concentrated to furnish 1-azido-2-methoxyethane as a yellow liquid. This azide (200 mg, 1.94 mmol) was added to a solution of 2-Amino-6-ethynylbenzonitrile (250 mg, 1.76 mmol) (Example 267c) in H2O/tert-BuOH=1:2 (15 mL) and the solution was treated consecutively with sodium ascorbate (0.264 mmol) and CuSO4 (0.035 mmol). The reaction mixture was stirred at room temperature for 48 hours, diluted with water and extracted with ethyl acetate. The organic extract was dried over MgSO4 and purified over silica gel (ethyl acetate/hexane 6:4) to furnish the title compound as a white solid in 88% yield. 1H NMR (400 MHz, DMSO-d6) δ 3.26 (s, 3H), 3.78 (t, J=5.2 Hz, 2H), 4.23 (t, J=5.2 Hz, 2H), 6.13 (br s, 2H), 6.80 (dd, J=1.2, 8.4 Hz, 1H), 7.09 (dd, J=1.2, 7.6 Hz, 1H), 7.36 (t, J=8.4 Hz, 1H), 8.52 (s, 1H). MS 244 (MH+). extracted with ethyl acetate The organic extract was dried over MgSO4 purified over silica gel (ethyl acetate/hexane 6:4)

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

实验步骤: To a solution of 1-bromo-2-methoxyethane (5.00 g, 35.97 mmol) in DMF (25 mL), was added sodium azide (3 equiv.) and the mixture was heated at 50° C. for 48 hours. The reaction mixture was diluted with water (75 mL) and extracted with diethyl ether. The organic extract was dried over MgSO4 and concentrated to furnish 1-azido-2-methoxyethane as a yellow liquid. This azide (200 mg, 1.94 mmol) was added to a solution of 2-Amino-6-ethynylbenzonitrile (250 mg, 1.76 mmol) (Example 267c) in H2O/tert-BuOH=1:2 (15 mL) and the solution was treated consecutively with sodium ascorbate (0.264 mmol) and CuSO4 (0.035 mmol). The reaction mixture was stirred at room temperature for 48 hours, diluted with water and extracted with ethyl acetate. The organic extract was dried over MgSO4 and purified over silica gel (ethyl acetate/hexane 6:4) to furnish the title compound as a white solid in 88% yield. 1H NMR (400 MHz, DMSO-d6) δ 3.26 (s, 3H), 3.78 (t, J=5.2 Hz, 2H), 4.23 (t, J=5.2 Hz, 2H), 6.13 (br s, 2H), 6.80 (dd, J=1.2, 8.4 Hz, 1H), 7.09 (dd, J=1.2, 7.6 Hz, 1H), 7.36 (t, J=8.4 Hz, 1H), 8.52 (s, 1H). MS 244 (MH+). extracted with ethyl acetate The organic extract was dried over MgSO4 purified over silica gel (ethyl acetate/hexane 6:4)

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

实验步骤: To a solution of 1-bromo-2-methoxyethane (5.00 g, 35.97 mmol) in DMF (25 mL), was added sodium azide (3 equiv.) and the mixture was heated at 50° C. for 48 hours. The reaction mixture was diluted with water (75 mL) and extracted with diethyl ether. The organic extract was dried over MgSO4 and concentrated to furnish 1-azido-2-methoxyethane as a yellow liquid. This azide (200 mg, 1.94 mmol) was added to a solution of 2-Amino-6-ethynylbenzonitrile (250 mg, 1.76 mmol) (Example 267c) in H2O/tert-BuOH=1:2 (15 mL) and the solution was treated consecutively with sodium ascorbate (0.264 mmol) and CuSO4 (0.035 mmol). The reaction mixture was stirred at room temperature for 48 hours, diluted with water and extracted with ethyl acetate. The organic extract was dried over MgSO4 and purified over silica gel (ethyl acetate/hexane 6:4) to furnish the title compound as a white solid in 88% yield. 1H NMR (400 MHz, DMSO-d6) δ 3.26 (s, 3H), 3.78 (t, J=5.2 Hz, 2H), 4.23 (t, J=5.2 Hz, 2H), 6.13 (br s, 2H), 6.80 (dd, J=1.2, 8.4 Hz, 1H), 7.09 (dd, J=1.2, 7.6 Hz, 1H), 7.36 (t, J=8.4 Hz, 1H), 8.52 (s, 1H). MS 244 (MH+). extracted with ethyl acetate The organic extract was dried over MgSO4 purified over silica gel (ethyl acetate/hexane 6:4)

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

实验步骤: To a solution of 1-bromo-2-methoxyethane (5.00 g, 35.97 mmol) in DMF (25 mL), was added sodium azide (3 equiv.) and the mixture was heated at 50° C. for 48 hours. The reaction mixture was diluted with water (75 mL) and extracted with diethyl ether. The organic extract was dried over MgSO4 and concentrated to furnish 1-azido-2-methoxyethane as a yellow liquid. This azide (200 mg, 1.94 mmol) was added to a solution of 2-Amino-6-ethynylbenzonitrile (250 mg, 1.76 mmol) (Example 267c) in H2O/tert-BuOH=1:2 (15 mL) and the solution was treated consecutively with sodium ascorbate (0.264 mmol) and CuSO4 (0.035 mmol). The reaction mixture was stirred at room temperature for 48 hours, diluted with water and extracted with ethyl acetate. The organic extract was dried over MgSO4 and purified over silica gel (ethyl acetate/hexane 6:4) to furnish the title compound as a white solid in 88% yield. 1H NMR (400 MHz, DMSO-d6) δ 3.26 (s, 3H), 3.78 (t, J=5.2 Hz, 2H), 4.23 (t, J=5.2 Hz, 2H), 6.13 (br s, 2H), 6.80 (dd, J=1.2, 8.4 Hz, 1H), 7.09 (dd, J=1.2, 7.6 Hz, 1H), 7.36 (t, J=8.4 Hz, 1H), 8.52 (s, 1H). MS 244 (MH+). extracted with ethyl acetate The organic extract was dried over MgSO4 purified over silica gel (ethyl acetate/hexane 6:4)