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| | (5-Bromo-pyridin-3-yl)-carbamic acid tert-butyl ester Basic information |
| Product Name: | (5-Bromo-pyridin-3-yl)-carbamic acid tert-butyl ester | | Synonyms: | TERT-BUTYL 5-BROMOPYRIDIN-3-YLCARBAMATE;tert-Butyl N-(5-broMopyridin-3-yl)carbaMate;5-(Boc-amino)-3-bromopyridine;tert-Butyl 5-bromopyridine-3-carbamate;5-Bromo-3-(Boc-amino)-pyridine;Carbamic acid, (5-bromo-3-pyridinyl)-, 1,1-dimethylethyl ester;Zinc04352716;Carbamic acid, N-(5-bromo-3-pyridinyl)-, 1,1-dimethylethyl ester | | CAS: | 361550-43-8 | | MF: | C10H13BrN2O2 | | MW: | 273.13 | | EINECS: | | | Product Categories: | | | Mol File: | 361550-43-8.mol |  |
| | (5-Bromo-pyridin-3-yl)-carbamic acid tert-butyl ester Chemical Properties |
| Melting point | 143-148°C | | Boiling point | 286.5±25.0 °C(Predicted) | | density | 1.453±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | pka | 12.26±0.70(Predicted) | | form | solid | | InChI | 1S/C10H13BrN2O2/c1-10(2,3)15-9(14)13-8-4-7(11)5-12-6-8/h4-6H,1-3H3,(H,13,14) | | InChIKey | MCNMZLIJAOGTJQ-UHFFFAOYSA-N | | SMILES | CC(C)(C)OC(=O)Nc1cncc(Br)c1 |
| Hazard Codes | Xi,Xn | | Risk Statements | 22 | | WGK Germany | 3 | | HazardClass | IRRITANT | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | (5-Bromo-pyridin-3-yl)-carbamic acid tert-butyl ester Usage And Synthesis |
| Synthesis | 5-Bromonicotinic acid (10 g, 49.5 mmol) was dissolved in tert-butanol (100 mL) at 20 °C and triethylamine (15.2 g, 150 mmol) and DPPA (20.4 g, 74 mmol) were added. The mixture was stirred in toluene (100 mL) at 65 °C for 40 min, followed by heating to 100 °C under nitrogen protection for 22 h of reaction. After completion of the reaction, the mixture was cooled and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane as eluent to afford tert-butyl 5-bromopyridine-3-carboxylate (10.52 g, 78%) as a white solid.1H NMR (300 MHz, CDCl3) δ 8.32 (m, 3H), 6.97 (brs, 1H), 1.53 (s, 9H); MS (ES) m/z: 273, 275 (M+H+). Calculated analytical value C10H13N2O2Br: C, 43.98; H, 4.80; N, 10.26. Measured value: C, 43.88; H, 4.52; N, 10.20. | | References | [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 695 - 709
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4535 - 4546
[3] Patent: WO2004/9562, 2004, A1. Location in patent: Page 31-33
[4] Patent: WO2006/82373, 2006, A1. Location in patent: Page/Page column 107
[5] Patent: US2008/194552, 2008, A1. Location in patent: Page/Page column 31 |
| | (5-Bromo-pyridin-3-yl)-carbamic acid tert-butyl ester Preparation Products And Raw materials |
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