tert-butyl 4-iodo-1H-pyrazole-1-carboxylate

4-Iodopyrazole (20 mmol) was treated with Etieri-Butyl 4-iodo-1 H-pyrazole-1 -carboxylate (2); [00189] 4-lodopyrazole (1) (7.85g 40.4mmole) was dissolved in THF (120ml_) and triethylamine (8.5ml_, 6.12g 60.5mmole) and di-terf-butyl dicarbonate (9.7g, 44.5mmole) were added. The reaction was stirred at r.t. for 3 hours. The THF was evaporated and ethyl acetate (100ml_) was added. The solution was washed with water (2x50ml_) and with brine, then dried and evaporated to leave an oil (14.2g). The crude product was purified by chromatography on a pad of silica in a sinter (10cm diam, 6cm thick) eluted with 10percent ethyl acetate in cyclohexane (1 1 x90ml_), then 20percent ethyl acetate in cyclohexane (3x90ml_) to give the protected pyrazole 2 (1 1 .66g 98percent). tert-Butyl 4-iodo-1H-pyrazole-1-carboxylate (2) In the reaction kettle, add 4 - iodine pyrazole (1.94 kg, 10 µM) and tetrahydrofuran 5 kg, stirring to dissolve, heating to the 20 - 30 °C, slow carbon acid di-tert-butyl adds by drops two (2.18 kg, 10 µM), drop the temperature increases slightly, the control temperature of not more than 35 °C. The completion of the dropping, stirring 1 - 2 hours, TLC confirms the completion of the reaction. The reaction liquid under reduced pressure when the distillation is carried out to the does not flow the fluid, adding 1.2 kg normal heptane cooling to 0 °C beating, filtering, drying to obtain N - BOC - 4 - iodine pyrazole 2.65 kg, yield 90percent, HPLC: 97.4percent.General procedure: To a solution of pyrazole 1-5 (1 equiv.) and triethylamine (1.5 equiv.) in dichloromethane (for 0.05mol of pyrazole – 50 mL of dichloromethane were user) Di-tert-butyl dicarbonate (1.2 equiv) wereadded at room temperature and left to stir overnight. Dichloromethane was washed with saturatedNaHCO3 solution (1×25 mL – for 50 mL of dichloromethane) then with deionized H2O (1 × 25mL). Organic layer was dried with anhydrous Na2SO4, and evaporated under reduced pressure.4-Iodopyrazole (20 mmol) was treated with Etieri-Butyl 4-iodo-1 H-pyrazole-1 -carboxylate (2); [00189] 4-lodopyrazole (1) (7.85g 40.4mmole) was dissolved in THF (120ml_) and triethylamine (8.5ml_, 6.12g 60.5mmole) and di-terf-butyl dicarbonate (9.7g, 44.5mmole) were added. The reaction was stirred at r.t. for 3 hours. The THF was evaporated and ethyl acetate (100ml_) was added. The solution was washed with water (2x50ml_) and with brine, then dried and evaporated to leave an oil (14.2g). The crude product was purified by chromatography on a pad of silica in a sinter (10cm diam, 6cm thick) eluted with 10percent ethyl acetate in cyclohexane (1 1 x90ml_), then 20percent ethyl acetate in cyclohexane (3x90ml_) to give the protected pyrazole 2 (1 1 .66g 98percent). tert-Butyl 4-iodo-1H-pyrazole-1-carboxylate (2) In the reaction kettle, add 4 - iodine pyrazole (1.94 kg, 10 µM) and tetrahydrofuran 5 kg, stirring to dissolve, heating to the 20 - 30 °C, slow carbon acid di-tert-butyl adds by drops two (2.18 kg, 10 µM), drop the temperature increases slightly, the control temperature of not more than 35 °C. The completion of the dropping, stirring 1 - 2 hours, TLC confirms the completion of the reaction. The reaction liquid under reduced pressure when the distillation is carried out to the does not flow the fluid, adding 1.2 kg normal heptane cooling to 0 °C beating, filtering, drying to obtain N - BOC - 4 - iodine pyrazole 2.65 kg, yield 90percent, HPLC: 97.4percent.General procedure: To a solution of pyrazole 1-5 (1 equiv.) and triethylamine (1.5 equiv.) in dichloromethane (for 0.05mol of pyrazole – 50 mL of dichloromethane were user) Di-tert-butyl dicarbonate (1.2 equiv) wereadded at room temperature and left to stir overnight. Dichloromethane was washed with saturatedNaHCO3 solution (1×25 mL – for 50 mL of dichloromethane) then with deionized H2O (1 × 25mL). Organic layer was dried with anhydrous Na2SO4, and evaporated under reduced pressure.

Molecular Weight:294.09
XLogP3:2.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:293.98653
Monoisotopic Mass:293.98653
Topological Polar Surface Area:44.1
Heavy Atom Count:13
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes