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| Product Name: | 1-(4-BOC-piperidyl)-4-iodopyrazole | | Synonyms: | 1-Piperidinecarboxylic acid, 4-(4-iodo-1H-pyrazol-1-yl)-, 1,1-dimethylethyl ester;Crizotinib Impurity 16;tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate;1-(4-BOC-piperazino)-4-iodopyrazole;1-(4-BOC-piperidyl)-4-iodopyrazole;1-Boc-4-(4-iodo-1H-pyrazol-1-yl)piperidine;4-(4-Iodo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester;tert-Butyl 4-(4-iodopyrazolyl)piperidinecarboxylate | | CAS: | 877399-73-0 | | MF: | C13H20IN3O2 | | MW: | 377.22 | | EINECS: | | | Product Categories: | | | Mol File: | 877399-73-0.mol |  |
| | 1-(4-BOC-piperidyl)-4-iodopyrazole Chemical Properties |
| Melting point | 97 °C | | Boiling point | 430.6±35.0 °C(Predicted) | | density | 1.60±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | form | Solid | | pka | 1.08±0.19(Predicted) | | Appearance | White to off-white Solid | | Sensitive | Light Sensitive | | InChI | InChI=1S/C13H20IN3O2/c1-13(2,3)19-12(18)16-6-4-11(5-7-16)17-9-10(14)8-15-17/h8-9,11H,4-7H2,1-3H3 | | InChIKey | IONGFFYQZADMPH-UHFFFAOYSA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCC(N2C=C(I)C=N2)CC1 |
| | 1-(4-BOC-piperidyl)-4-iodopyrazole Usage And Synthesis |
| Uses | 4-(4-iodo-1H-pyrazol-1-yl)-1-piperidinecarboxylic acid-1,1-dimethyl ethyl ester is a useful research chemical. | | Application | 4-(4-iodo-1H-pyrazol-1-yl)-1-piperidinecarboxylic acid-1,1-dimethyl ethyl ester is an organic heterocyclic compound that can be used as a pharmaceutical intermediate. | | Synthesis | 1-(4-BOC-piperidyl)-4-iodopyrazole is prepared by the reaction of 4-Iodopyrazole and 1-Boc-4-methanesulfonyloxypiperidine. The specific synthesis steps are as follows:
To a stirred solution of 4-iodo-lH-pyrazole (8.98 g, 46.28 mmol) in DCM (160 mL) was added NaH (1.67 g, 55.53 mmol, 80percent NaH/mineral oil) portion-wise at 0 °C. The mixture was stirred at 0 °C for 1 hour, then tert-butyl 4-((methylsulfonyl)oxy)piperidine-l- carboxylate (14.22 g, 50.90 mmol) was added. The resulted mixture was stirred at 100 °C for 15 hours, then cooled to rt, quenched with H20 (30 mL) and concentrated in vacuo. The residue was diluted with H20 (150 mL), and the mixture was extracted with EtOAc (100 mL x 5). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 5/1) to give 1-(4-BOC-piperidyl)-4-iodopyrazole as a white solid (12.25 g, 70.2percent>). MS (ESI, pos. ion) m/z: 322.0 (M-56+1).
 | | References | [1] Patent: WO2014/193647, 2014, A2. Location in patent: Paragraph 0184
[2] Patent: CN104119331, 2018, B. Location in patent: Paragraph 0382; 0387; 0388
[3] Patent: EP2650293, 2013, A1. Location in patent: Paragraph 0195; 0196
[4] Patent: US2008/300273, 2008, A1
[5] Patent: US2008/293769, 2008, A1. Location in patent: Page/Page column 6 |
| | 1-(4-BOC-piperidyl)-4-iodopyrazole Preparation Products And Raw materials |
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