Category: 1150271-23-0

Synthetic Route of 1150271-23-0, These common heterocyclic compound, 1150271-23-0, name is tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

tert-Butyl 4-bromopyrazole-1-carboxylate (230 mg, 0.931 mmol), tert-butyl 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate (250 mg, 0.847 mmol) and potassium carbonate (1.3 mL of 2M, 2.60 mmol) were combined in dioxane (3 mL) and the mixture de-gassed (x 2 vacuum cycles). Pd(dppf)Cl2.DCM (70 mg, 0.086 mmol) was added and the mixture de-gassed (x 2 vacuum cycles) then heated at 90 C overnight. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried (Na2SO4), filtered and concentraed in vacuo. The residue was purified by chromatography (silica, 0-100% EtOAc/Petroleum ether gradient elution). Product fractions were combined and concentrated to give the product as a pale yellow film (65 mg, 33%) that was taken on to the next reaction. ESV- MS m/z 236.0 (M+1) +.

Statistics shows that tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 1150271-23-0.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BLEICH, Matthew; CHARRIER, Jean-Damien; DONG, Huijun; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KNEGTEL, Ronald; MOCHALKIN, Igor; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; QIU, Hui; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (312 pag.)WO2019/148136; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1150271-23-0, These common heterocyclic compound, 1150271-23-0, name is tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In the reaction kettle, adding tetrahydrofuran 4.5 kg and 1 – BOC – 4 – brompyrazole (2.01 kg, 9.2 muM), 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 muM) 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 muM) 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: 99.1%, HNMR consistent with the literature value, yield 76%.

The synthetic route of 1150271-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cangzhou Puri Oriental Technology Co., Ltd; Leng, Yanguo; Gui, Qian; Shen, Haibing; (5 pag.)CN106188116; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1150271-23-0, These common heterocyclic compound, 1150271-23-0, name is tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred degassed solution of 4-bromo-pyrazole-1 -carboxylic acid tert- butyl ester (300 mg, 1 .21 mmol) in DMF (3 mL) were added phenyl acetylene (0.24 ml_, 2.18 mmol), triethyl amine (0.84 mL, 6.05 mmol), Cul (40.16 mg, 0.24 mmol) followed by Pd(PPh3)4 (279.58 mg, 0.24 mmol). Resulting reaction mixture was heated at 70C for 6 hours. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. Combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. Crude compound was purified by column chromatography (10-20% ethyl acetate in hexane) to get tert-butyl 4-(2-phenylethynyl)-1 H-pyrazole-1-carboxylate (230 mg, 70%) as brown liquid. MS (ESI): m/z 269.3 [M+1]+.

The synthetic route of 1150271-23-0 has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 1150271-23-0, name is tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate, molecular formula is C8H11BrN2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 1150271-23-0

Add 1-Boc-4-bromopyrazole (24.7 g, 0.1 mol), bis(pinacolato)diboron (25.4 g, 0.1 mol) and catalyst [1,1′-bis (diphenylphosphino) ferrocene ] Palladium dichloride (0.74 g, 0.001 mol), potassium acetate (19.6 g, 0.2 mol), 200 ml of ethanol were added to the reaction bottle, and after removing the oxygen under reduced pressure, the nitrogen was heated to reflux, and the reaction was held for 16 hours. After monitoring the reaction of the raw materials, the filtrate was filtered. The filtrate was distilled off ethanol under reduced pressure. The residue was extracted with petroleum ether and purified to obtain 24.2 g of 1-Boc-4-pyrazoleboronic acid pinacol ester with a yield of 82.3%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1150271-23-0, its application will become more common.