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| | 6-Bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester Basic information |
| Product Name: | 6-Bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | | Synonyms: | 2-Boc-6-bromo-3,4-dihydro-1H-isoquinoline;tert-butyl 6-broMo-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;2-Boc-6-bromo-1,2,3,4-tetrahydroisoquinoline;N-BOC-6-bromo-3,4-dihydroisoquinoline;tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H);6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline;2(1H)-Isoquinolinecarboxylic acid, 6-bromo-3,4-dihydro-, 1,1-dimethylethyl ester;tert-butyl 6-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylate | | CAS: | 893566-74-0 | | MF: | C14H18BrNO2 | | MW: | 312.2 | | EINECS: | | | Product Categories: | CHIRAL CHEMICALS | | Mol File: | 893566-74-0.mol |  |
| | 6-Bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester Chemical Properties |
| Boiling point | 374.2±42.0 °C(Predicted) | | density | 1.353±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | pka | -1.56±0.20(Predicted) | | Appearance | Colorless to light yellow Solid-Liquid Mixture | | InChI | InChI=1S/C14H18BrNO2/c1-14(2,3)18-13(17)16-7-6-10-8-12(15)5-4-11(10)9-16/h4-5,8H,6-7,9H2,1-3H3 | | InChIKey | SZIPGDGOBMFCEH-UHFFFAOYSA-N | | SMILES | C1C2=C(C=C(Br)C=C2)CCN1C(OC(C)(C)C)=O |
| | 6-Bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester Usage And Synthesis |
| Synthesis | Di-tert-butyl dicarbonate (3.52 g, 16.14 mmol) was slowly added to a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (3.26 g, 15.37 mmol) in tetrahydrofuran (45 mL) at room temperature. The reaction mixture was stirred continuously for 15 h at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using solvent gradient elution (0→8% ethyl acetate/hexane) to afford the target compound tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (5.05 g, 16.18 mmol, quantitative yield) as a colorless oil.1H NMR (300 MHz, CDCl3) δ: 1.49 (9H, s) ), 2.80 (2H, t, J = 5.9 Hz), 3.62 (2H, t, J = 5.9 Hz), 4.51 (2H, s), 6.97 (1H, d, J = 8.7 Hz), 7.28-7.32 (2H, m). | | References | [1] Patent: EP3192791, 2017, A1. Location in patent: Paragraph 0594
[2] ChemMedChem, 2018, vol. 13, # 14, p. 1405 - 1413
[3] Patent: WO2013/80222, 2013, A1. Location in patent: Page/Page column 40
[4] Patent: WO2017/184662, 2017, A1. Location in patent: Page/Page column 58
[5] Patent: WO2017/68412, 2017, A1. Location in patent: Page/Page column 274 |
| | 6-Bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester Preparation Products And Raw materials |
| Raw materials | 6-Bromoisoquinoline-->6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride-->6-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline-->3-Bromophenethylamine-->6-bromo-1,2,3,4-tetrahydroisoquinoline-->Di-tert-butyl dicarbonate-->3-Bromophenylacetonitrile | | Preparation Products | tert-Butyl 8-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate |
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