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[ CAS No. 1150271-23-0 ]

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Chemical Structure| 1150271-23-0
Chemical Structure| 1150271-23-0
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CAS No. :1150271-23-0 MDL No. :MFCD09999163
Formula : C8H11BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :247.09 g/mol Pubchem ID :45789723
Synonyms :

Safety of [ 1150271-23-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1150271-23-0 ]

  • Upstream synthesis route of [ 1150271-23-0 ]
  • Downstream synthetic route of [ 1150271-23-0 ]

[ 1150271-23-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 557087-01-1 ]
  • [ 1150271-23-0 ]
  • [ 269410-08-4 ]
YieldReaction ConditionsOperation in experiment
76% With n-Bu3MgLi In tetrahydrofuran at -20 - -10℃; Large scale In the reaction kettle, adding tetrahydrofuran 4.5 kg and 1 - BOC - 4 - brompyrazole (2.01 kg, 9.2 µM), stirring 0.5 hours, cooling to -20 °C, maintain -10 °C -0 °C dropwise 3.2molBu3MgLi [preparation method: 1.0eq butyl magnesium chloride in -10 °C -0 °C lower drop by adding 2.0 equivalent butyl lithium in], TLC detection reaction, maintain the exchange completion -10 °C -0 °C dropwise dimethylamine fundamental frequency that mellow boron ester (1.61 kg, 9.4 µM) dissolved in 1 kg of the mixed solution in tetrahydrofuran, the completion of the dropping, thermal insulation 2 hours, natural heating stirring overnight. The control temperature of not more than 30 °C after adding glacial acetic acid, after detecting the protecting group removal, stop stirring filtration, the mother liquor recovered, solid add triethylamine (1.01 kg, 10 µM) and ethyl acetate 8 kg after, heating to reflux reaction, the proportion of internal standard detecting product is not increased when, after lowering the filtering, the filtrate obtained after the distillation is a kind of white solid, by adding heptane cooling to 0 °C beating, filtering, 50 - 60 °C vacuum drying to obtain white solid pyrazole -4 - boric acid frequency that alcohol ester 1.36 kg, GC: 99.1percent, HNMR consistent with the literature value, yield 76percent.
Reference: [1] Patent: CN106188116, 2016, A, . Location in patent: Paragraph 0016; 0017
  • 2
  • [ 2075-45-8 ]
  • [ 24424-99-5 ]
  • [ 1150271-23-0 ]
YieldReaction ConditionsOperation in experiment
98% With dmap; triethylamine In acetonitrile at 20℃; for 2 h; Step 1: Preparation of tert-butyl 4-bromo-lH-pyrazole-l-carboxylate B [00161] Boc anhydride (2.34 niL, 10.2 mmol) was added to a solution of 4-bromo-lH- pyrazole (1 g, 6.8 mmol), triethylamine (3.3 raL, 23.8 mmol) and 4-dimethylaminopyridine (0.166 g, 1.36 mmol) in acetonitrile (20 mL) at 0 °C and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water and extracted with ethyl acetate (100 niL x 3). The combined organic extract was washed with water (100 mL), brine (100 raL), dried over anhydrous sodium sulfate and evaporated. The crude material was purified by combiflash purifier using 10percent ethyl acetate in hexane to afford the title compound tert-butyl 4- bromo-1 H-pyrazole- 1 -carboxylate (1.65 g, 98percent yield) as a colorless liquid. FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDCls) δ 8.09 (s, 1H), 7.66 (s, 1H), 1.65 (s, 9H).
93% With triethylamine In dichloromethane at 20℃; 4-Bromo-1H-pyrazole, 5.00 g (34.0 mmol), di-tert-butyl dicarbonate, 8.17 g (37.4 mmol), and triethylamine, 7.57 g (74.8 mmol), were added into 50 mL of dichloromethane. The resulting mixture was stirred at room temperature for overnight. The resulting mixture was purified by silica gel column chromatography to give 8.00 g (93percent) of the product as an off-white solid. MS (ESIpos): m/z = 247 [M+H]+. LC-MS [method 4, gradient starting with water (0.1 percentHCOOH)-Acetonitrile, 10percentB]: Rt = 1.75 min.
92% at 30 - 45℃; Large scale In the reaction kettle, add 4 - brompyrazole (1.47 kg, 10 µM) and tetrahydrofuran 6 kg, stirring to dissolve, heating to 30 - 40 °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 45 °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 - brompyrazole 2.01 kg, yield 92percent, HPLC: 98.3percent.
86% With triethylamine In dichloromethane at 25℃; for 1 h; To a mixture of 4-bromo- lH-pyrazole (500 mg, 3.40 mmol) in DCM (10 mL) was added Boc20 (0.790 mL, 3.40 mmol) and Et3N (0.948 mL, 6.80 mmol). The mixture was stirred at 25 °C for 1 h. The mixture was concentrated to afford fert-butyl 4-bromo- lH-pyrazole-l-carboxylate (800 mg, 2.91 mmol, 86percent yield). TLC (PE/EA = 2: 1, Rf = 0.6): lH NMR (400 MHz, CD3OD) δ 8.31 (s, 1H), 7.77 (s, 1H), 1.63 (s, 9H). ES-LCMS m/z 148.0 (M-Boc+H).
79.6% With triethylamine In dichloromethane at 20℃; 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.

Reference: [1] Patent: WO2016/49165, 2016, A1, . Location in patent: Paragraph 00161
[2] Patent: WO2018/172250, 2018, A1, . Location in patent: Page/Page column 300
[3] Patent: CN106188116, 2016, A, . Location in patent: Paragraph 0016
[4] Patent: WO2014/141187, 2014, A1, . Location in patent: Page/Page column 142
[5] Arkivoc, 2014, vol. 2014, # 6, p. 54 - 71
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