Alternatived Products of [ 433969-27-8 ]
Product Details of [ 433969-27-8 ]
| CAS No. : | 433969-27-8 |
MDL No. : | MFCD05663974 |
| Formula : |
C12H18BNO4
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | NVCGSIBAXVRMLU-UHFFFAOYSA-N |
| M.W : |
251.09
|
Pubchem ID : | 10911965 |
| Synonyms : |
|
Safety of [ 433969-27-8 ]
Application In Synthesis of [ 433969-27-8 ]
* 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 [ 433969-27-8 ]
- 1
-
[ 162356-90-3 ]
-
[ 433969-27-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 100% |
Multistep reaction.; |
|
| 92% |
Stage #1: N-(tert-butoxycarbonyl)-2-bromobenzylamine With methyllithium; tert.-butyl lithium In tetrahydrofuran; diethyl ether; pentane at -78℃; for 2h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; diethyl ether; pentane at -78 - 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether; pentane |
|
|
With Triisopropyl borate Inert atmosphere; |
|
Reference：
[1]Peukert, Stefan; Brendel, Joachim; Pirard, Bernard; Brüggemann, Andrea; Below, Peter; Kleemann, Heinz-Werner; Hemmerle, Horst; Schmidt, Wolfgang
[Journal of Medicinal Chemistry, 2003, vol. 46, # 4, p. 486 - 498]
[2]Boudreault, Pierre-Luc; Cardinal, Sébastien; Voyer, Normand
[Synlett, 2010, # 16, p. 2449 - 2452]
[3]Tricotet, Thomas; Fleming, Patricia; Cotter, Juliet; Hogan, Anne-Marie L.; Strohmann, Carsten; et al.
[Journal of the American Chemical Society, 2009, vol. 131, p. 3142 - 3143]
- 2
-
[ 5419-55-6 ]
-
[ 162356-90-3 ]
-
[ 433969-27-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 98% |
Stage #1: N-(tert-butoxycarbonyl)-2-bromobenzylamine With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; Inert atmosphere;
Stage #2: With tert.-butyl lithium In tetrahydrofuran; diethyl ether; hexane at -78℃; for 1h; Inert atmosphere;
Stage #3: Triisopropyl borate Further stages; |
|
| 98% |
Stage #1: N-(tert-butoxycarbonyl)-2-bromobenzylamine With methyllithium; tert.-butyl lithium In tetrahydrofuran; diethyl ether; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: Triisopropyl borate In tetrahydrofuran; diethyl ether; hexane at 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; diethyl ether; hexane; water |
1 2-(tert-Butoxycarbonylaminomethyl)phenylboronic Acid (precursor 2).
Precursor 1 (4.28 g, 15.0 mmol) was added to anhydrous THF (15 mL) under a nitrogen atmosphere and cooled to -78 °C. 1.4 M of MeLi in ether (13.4 mL, 18.75 mmol) was then added via syringe and the resulting mixture was stirred for 1 hour, after which 1.6 M tert-BuLi in hexanes (22.5 mL, 36 mmol) was added and the resultingsolution was stirred for an additional hour. Triisopropyl borate (13.85 mL, 60 mmol) was then added and the solution was then allowed to warm to room temperature. The reaction mixture was stirred overnight at room temperature and then diluted with 1 M HC1 to a pH of 6. The reaction mixture was then extracted with CH2C12 and the organicphase was washed with water and saturated NaC1. The organic layer was then dried using sodium sulfate and concentrated in vacuo to give the title compound: yield 98%. |
Reference：
[1]Baczko, Istvan; Liknes, David; Yang, Wei; Hamming, Kevin C.; Searle, Gavin; Jaeger, Kristian; Husti, Zoltan; Juhasz, Viktor; Klausz, Gergely; Pap, Robert; Saghy, Laszlo; Varro, Andras; Dolinsky, Vernon; Wang, Shaohua; Rauniyar, Vivek; Hall, Dennis; Dyck, Jason R.B.; Light, Peter E.
[British Journal of Pharmacology, 2014, vol. 171, # 1, p. 92 - 106]
[2]Current Patent Assignee: UNIVERSITY OF ALBERTA; CENTRE FOR DRUG RESEARCH AND DEVELOPMENT - WO2014/183221, 2014, A1
Location in patent: Paragraph 00168
- 3
-
[ 374554-54-8 ]
-
[ 433969-27-8 ]
-
C21H23N3O2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 240 mg |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 1.5h;Inert atmosphere; |
To a solution of compound A20 (300 mg, 1.68 mmol) and compound A19 (506 mg, 2.02 mmol) in dioxane (5 mL) and H20 (1 mL) was added CS2CO3 (547 mg, 1.68 mmol), Pd(dppf)Cl2 (123 mg, 0.168 mmol) under N2. The resulting mixture was heated at l00C and stirred for 1.5 hours to give black suspension. LCMS and TLC showed the reaction was completed. The reaction mixture was quenched by addition H20 (50 mL) and extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine (20 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by combi flash to give compound A21 (240 mg) as a yellow solid. |
- 4
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[ 4225-86-9 ]
-
[ 433969-27-8 ]
-
C21H21N3O4
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 1 g |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 16.0h;Inert atmosphere; |
To a solution of compound B19 (560 mg, 2.68 mmol) and compound B20 (2.02 g, 8.04 mmol) in dioxane (10 mL) / H20 (3 mL) was added CS2CO3 (1.75 g, 5.36 mmol) and Pd(dppf)Cl2 (98.1 mg, 0.134 mmol) under N2 atmosphere. The reaction mixture was heated to l00C and stirred for 16 hours under N2 atmosphere to give a black mixture. TLC showed the reaction was completed. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (200 mL x 2). The combined extracts were dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by Combi Flash to give compound B21 (1.00 g) as brown solid. |
- 5
-
[ 347146-33-2 ]
-
[ 433969-27-8 ]
-
C21H23N3O2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 1 g |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100.0℃; for 4.0h;Inert atmosphere; |
To a solution of compound B28 (1.00 g, 5.60 mmol) and compound B29 (4.22 g, 16.8 mmol) in dioxane (15 mL) / H20 (5 mL) was added Cs2C03 (3.65 g, 11.2 mmol) and Pd(dppf)Cl2 (205 mg, 0.280 mmol) under N2 atmosphere. The reaction mixture was heated to l00C and stirred for 4 hours under N2 atmosphere to give a black mixture. TLC showed the reaction was completed. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (200 mL x 2). The combined extracts were dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by Combi Flash to give compound B30 (1.00 g) as black brown oil. |
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