Alternatived Products of [ 168169-11-7 ]
Product Details of [ 168169-11-7 ]
| CAS No. : | 168169-11-7 |
MDL No. : | MFCD08704822 |
| Formula : |
C15H16BrNO2
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Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : | 322.20 g/mol |
Pubchem ID : | - |
| Synonyms : |
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Safety of [ 168169-11-7 ]
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Application In Synthesis of [ 168169-11-7 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 168169-11-7 ]
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[ 24424-99-5 ]
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[ 2298-07-9 ]
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[ 168169-11-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 96h; |
4-Bromo-l-naphthylamine (5.0g, 22.5 mmol) and ditertbutyldicarbonate (7.4 g, 33.9 mmol) in tetrahydrofuran (75 ml) and 1Msodium hydroxide (75 ml) are stirred at room temperature for 4 days. The mixture is thenpoured into ethyl acetate (250 ml) and washed with water (300 ml). The ethyl acetate layer isdried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified bycolumn chromatography on silica gel eluted with 10% ethyl acetate in hexanes thenrecrystalized from ethyl acetate and hexanes to yield (4-bromo-naphthalen-l-yl)-carbamic acidtert-butyl ester (3.669 g). |
Reference：
[1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7089 - 7110
[2]Chemistry - A European Journal,2016,vol. 22,p. 1484 - 1492
[3]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2599 - 2606
[4]Patent: WO2006/10082,2006,A1 .Location in patent: Page/Page column 132-133
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[ 168169-11-7 ]
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[ 304873-65-2 ]
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[ 1338815-52-3 ]
| Yield | Reaction Conditions | Operation in experiment |
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Intermediate F1 : (4-(ierf-Butoxycarbonyl)aminonaphthalen-1 -yl)(2-(ferf-butoxy carbonyl)aminopyridin-4-yl)methanol.To a stirred solution of ie t-butyl (4-bromonaphthalen-1-yl)carbamate (WO 2006/010082) (2.09 g, 6.48 mmol) in dry THF (50 mL) under N2 at -78C was added n-butyllithium (2.5 M in hexanes, 5.5 mL, 13.8 mmol) over 15 mins. The resulting mixture was maintained at -78 C for 1.5 hr and then treated with a solution of ierf-butyl (4-formylpyridin-2-yl)carbamate (WO 2004/000831 ) (960 mg, 4.30 mmol) in dry THF (10 mL) in one portion. The reaction mixture was stirred at -78 C for a further 1 hr and then warmed to RT for 18 hr. The mixture was cooled to 0C and the reaction was quenched by the addition of MeOH (5.0 mL), then warmed to RT and partitioned between EtOAc and water. The aq layer was separated and was extracted twice with EtOAc and the combined organic extracts were washed with brine and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 80 g, EtOAc in isohexane, 0-60%, gradient elution) to afford the title compound, Intermediate F1 , as a pale yellow solid (1.13g, 88% purity (LCMS), 49%); Rt 2.22 min (Method 2); m/z 466 (M+H)+ (ES+). The material so obtained was used in the next step without further purification. |
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