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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (10g) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3* 150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. (0657) NMR (400MHz, CDCIs) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1.57-1.49 (m, 6H) 1.37-1.29 (m, 6H) 1.19-1.13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
16.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 m_) at -78°C under nitrogen was added a solution of pyridazine (10 g) and tri-n-butyltin chloride (44.6 g) in THF (100 ml_) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford (0834) tributyl(pyridazin-4-yl)stannane as a pale brown liquid. NMR (400MHz, CDCIs) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1.57-1.49 (m, 6H) 1.37-1.29 (m, 6H) 1.19-1.13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (10 g) and tri-n-butyltin chloride (44.6 g) in tetrahydrofuran (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. NMR (400MHz, CDCIs) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°Cunder nitrogenwas added a solution of pyridazine (1 Og) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. NMR (400MHz, CDCb) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (1 Og) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. NMR (400MHz, CDCb) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (1 Og) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. (0255) NMR (400MHz, CDCb) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
2.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 ml_) at -78°Cunder nitrogenwas added a solution of pyridazine (10 g) and tri-n-butyltin chloride (44.6 g) in tetrahydrofuran (100 ml_) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 ml_) and extracted with ethyl acetate (3x150 ml_). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. NMR (400MHz, CDCI3) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H) |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 ml_) at -78°C, under nitrogen atmosphere, was added a solution of pyridazine (10 g) and tri-n-butyltin chloride (44.6 g) in tetrahydrofuran (100 ml_) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 ml_) and extracted with ethyl acetate (3x150 ml_). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. NMR (400MHz, CDCI3) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1.57-1.49 (m, 6H) 1.37-1.29 (m, 6H) 1.19-1.13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (1 Og) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. NMR (400MHz, CDCb) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
3.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (10g) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. (0480) NMR (400MHz, CDCb) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H) |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (125 ml_, 1 M solution in tetrahydrofuran) at -78°C was added a solution of pyridazine (10g) and tri-n-butyltin chloride (44.6 g) in THF (100 ml_) drop wise under a nitrogen atmosphere. The reaction mixture was stirred at -78°C for 1 hour, then warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 ml_) and extracted with ethyl acetate (3x150 ml_). The combined organic layers were dried over sodium sulfate, concentrated and purified by silica gel chromatography eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. (0666) NMR (400MHz, CDCb) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H) |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (1 Og) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. 1 H NMR (400MHz, CDCl3) 9.17 (t, 1H) 9.02 (dd, 1H) 7.54 (dd, 1H) 1.57-1.49 (m, 6H) 1.37-1.29 (m, 6H) 1.19-1.13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 ml_) at -78°C under nitrogen was added a solution of pyridazine (10g) and tri-n-butyltin chloride (44.6g) in THF (100 ml_) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 ml_) and extracted with ethyl acetate (3x150 ml_). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. (0510) NMR (400MHz, CDCb) 9.17 (t, 1 H) 9.02 (dd, 1 H) 7.54 (dd, 1 H) 1 .57-1 .49 (m, 6H) 1 .37-1 .29 (m, 6H) 1 .19-1 .13 (m, 6H) 0.92-0.86 (m, 9H). |
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With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; |
1.1 Step 1 : Preparation of tributyl(pyridazin-4-yl)stannane
To a solution of lithium diisopropylamide (1 M solution in tetrahydrofuran, 125 mL) at -78°C under nitrogen was added a solution of pyridazine (1 Og) and tri-n-butyltin chloride (44.6g) in THF (100 mL) drop wise. The reaction mixture was stirred at -78°C for 1 hour. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3x150 mL). The organic layer was dried over sodium sulfate, concentrated and purified by chromatography on silica eluting with 30% ethyl acetate in hexanes to afford tributyl(pyridazin-4-yl)stannane as a pale brown liquid. 1 H NMR (400MHz, CDCl3) 9.17 (t, 1H) 9.02 (dd, 1H) 7.54 (dd, 1H) 1.57-1.49 (m, 6H) 1.37-1.29 (m, 6H) 1.19-1.13 (m, 6H) 0.92-0.86 (m, 9H). |
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