4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester Basic information
- Product Name:
- 4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
- Synonyms:
-
- 4-(4-Bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester
- Crizotinib Impurity 4
- CRIXOTINIB-D
- 4-Bromo-1-(N-boc-piperidin-4-yl)-1H-pyrazole
- 1-Boc-4-(4-bromo-1-pyrazolyl)piperidine
- 1-(4-BOC-Piperidino)-4-bromopyrazole
- (R)-5-broMo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-a
- 1-Boc-4-(4-broMopyrazol-1-yl)piperidine
- CAS:
- 877399-50-3
- MF:
- C13H20BrN3O2
- MW:
- 330.22
- Product Categories:
-
- intermediate
- API intermediates
- Mol File:
- 877399-50-3.mol
4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester Chemical Properties
- Melting point:
- 77.0 to 81.0 °C
- Boiling point:
- 411.5±35.0 °C(Predicted)
- Density
- 1.43
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- soluble in Methanol
- form
- Solid
- pka
- 0.92±0.19(Predicted)
- color
- Off-white
- CAS DataBase Reference
- 877399-50-3
4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester Usage And Synthesis
Synthesis
2075-45-8
141699-59-4
877399-50-3
General procedure for the synthesis of tert-butyl 4-(4-bromopyrazol-1-yl)piperidine-1-carboxylate from 4-bromopyrazole and tert-butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate: 2.08 kg of cesium carbonate and 0.78 kg of 4-bromopyrazole were dissolved in 4 liters of N-methyl pyrrolidinone, and heated to 80°C. Subsequently, 2.08 kg of cesium carbonate and 0.78 kg of 4-bromopyrazole were dissolved in 5 liters of N-methyl pyrrolidinone. 1.8 kg of tert-butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate was added to the reaction mixture and the reaction lasted for 12 hours. After completion of the reaction, it was cooled to room temperature, 50 liters of methyl tert-butyl ether and 50 liters of water were added and stirred for 1 hour. After separating the organic phase, the organic phase was washed 4 times with 20 liters of water, then dried with 50% hexane and stirred for 2 hours at room temperature. Finally, it was filtered and dried to give 1.35 kg of tert-butyl 4-(4-bromopyrazol-1-yl)piperidine-1-carboxylate in 77% yield.
References
[1] Patent: CN106317024, 2017, A. Location in patent: Paragraph 0060; 0061
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 12, p. 4092 - 4108
[3] Patent: WO2015/81257, 2015, A2. Location in patent: Page/Page column 81
[4] Tetrahedron Letters, 2014, vol. 55, # 9, p. 1528 - 1531
[5] Patent: US2006/46991, 2006, A1. Location in patent: Page/Page column 64-65
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4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester(877399-50-3)Related Product Information
- Tris(trimethylsilyl)phosphate
- tert-Butyl carbazate
- 2-Butoxyethanol
- Butylparaben
- Butyl acetate
- Isobutyl chloroformate
- tert-Butyl bromoacetate
- Methyl acrylate
- Diisobutyl phthalate
- Butyl acrylate
- tert-Butyl peroxybenzoate
- Butyl benzoate
- Buprofezin
- Piperidine
- 4-Bromopyrazole
- TERT-BUTYL FORMATE
- 4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
- CARBOXYLIC ACID