Alternatived Products of [ 133311-51-0 ]
Product Details of [ 133311-51-0 ]
| CAS No. : | 133311-51-0 |
MDL No. : | MFCD11109488 |
| Formula : |
C9H6BrNS
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | DQKKZVBNEAECJZ-UHFFFAOYSA-N |
| M.W : | 240.12 |
Pubchem ID : | 10728723 |
| Synonyms : |
|
Safety of [ 133311-51-0 ]
Application In Synthesis of [ 133311-51-0 ]
* 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 [ 133311-51-0 ]
- 1
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[ 3034-48-8 ]
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[ 71-43-2 ]
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[ 133311-51-0 ]
- 2
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[ 39136-63-5 ]
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[ 7758-99-8 ]
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[ 133311-51-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 18.6 parts (98.0%) |
With sodium bromide; phosphoric acid; nitric acid; sodium nitrite; In water; |
Example 7 To a stirred and cooled (-10C) solution of 13.9 parts of <strong>[39136-63-5]5-phenyl-2-thiazolamine</strong> (this product is described in J. Am. Chem. Soc. 71 , 4007, 1949) and 119 parts of phosphoric acid were added dropwise 37.5 parts of nitric acid. Upon complete addition, a solution of 7.85 parts of sodium nitrite in 12.4 parts of water was added dropwise during 35 minutes at -5C. Upon completion, the thus obtained solution was added dropwise to a cooled (-5C) mixture of 13.2 parts of copper(II)sulfate, 51.4 parts of sodium bromide and 275 parts of water. Upon completion, the reaction mixture was allowed to stand overnight to reach room temperature. The whole was neutralized with sodium carbonate (exothermic reaction, the temperature rose to 40C). After cooling, the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 18.6 parts (98.0%) of 2-bromo-5-phenylthiazole as a residue (interm. 19). |
- 3
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[ 18503-89-4 ]
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[ 133311-51-0 ]
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[ 75427-04-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 61% |
With 5 wt% ruthenium/carbon; lithium tert-butoxide at 8℃; for 8h; |
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- 4
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[ 39136-63-5 ]
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[ 133311-51-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 2 g |
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To a solution of <strong>[39136-63-5]5-phenylthiazol-2-amine</strong> (10.0 g, 56.8 mmol) in MeCN (200 ml) was added CuBr2 (15.2 g, 68.18 mmol) at 0C and stirred for 10 mm. Tert-butyl nitrite (8.10 ml, 68.2 mmol) was added drop wise to the reaction mixture at 0C. The reaction mixture was stirred at rt for 2 h. The resulting reaction mixture filtered through celite hyflow. The celite cake was washed with MeCN (2 x 100 ml). The filtrate was concentrated under reduced pressure and diluted with water (100 ml). The resulting mixture was extracted with EtOAc (3 x 80 ml). The combined organic phase was collected,dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (30% EtOAc in hexane) yielding 2-bromo-5-phenylthiazole (2.00 g, 8.33 mmol). LCMS: Method B, 4.78 mi MS: ES+ 240.20; ?H NMR (400 MHz, DMSO-d6) ppm 8.13 (s, 1 H), 7.65 - 7.67 (m, 2 H), 7.45 - 7.49 (m, 2 H), 7.39 - 7.43 (m, 1 H). |
- 5
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[ 199174-29-3 ]
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[ 133311-51-0 ]
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tert-butyl (R)-3-(((5-phenylthiazol-2-yl)amino)methyl)pyrrolidine-1-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 0.12 g |
In ethanol; at 100℃; for 120h; |
To a solution of 2-bromo-5-phenylthiazole (0.30 g, 1.24 mmol) in EtOH (5 ml) was added <strong>[199174-29-3]tert-butyl (R)-3-(aminomethyl)pyrrolidine-1-carboxylate</strong> (0.274 g, 1.36 mmol) at rt. The reaction mixture was heated at 100C for 120 h. The resulting reaction mixture was cooled to rt and concentrated under reduced pressure. The crude residue was purified by column chromatography (40% EtOAc in hexane) yielding tert-butyl (R)-3 -(((5 -phenylthiazol-2-yl)amino) methyl)pyrrolidine1-carboxylate (0.12 g, 0.33 mmol). LCMS: Method B, 4.27 mi MS: ES+ 360.43. |
- 6
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[ 1895006-01-5 ]
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[ 133311-51-0 ]
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[ 2229831-44-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 63% |
With copper(I) thiophene-2-carboxylate; 4,7-dimethoxy-1,10-phenanthroline; 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-trisilanol; [Ir(2-(2,4-difluorophenyl)-5-(methyl)pyridinyl)2(4,4′-bis(tert-butyl)bipyridine)]*PF6; sodium carbonate In acetone at 35℃; Irradiation; |
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- 7
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[ 186203-81-6 ]
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[ 133311-51-0 ]
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tert-butyl 1-(5-phenylthiazol-2-yl)octahydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 0.163 g |
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; CyJohnPhos; In toluene; at 20 - 110℃; for 16.0h;Inert atmosphere; |
Step a. To a solution of 2-bromo-5-phenylthiazole (CAS Number 133311-51-0; 0.158 g, 0.660 mmol) in toluene (5 ml) was added <strong>[186203-81-6]tert-butyl octahydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate</strong> (CAS Number 186203-81-6; 0.150 g, 0.660 mmol) at rt. Sodium tert-butoxide (0.120 g, 1.30 mmol) was added to the reaction mixture at rt. The resulting reaction mixture was degassed for 15 min and then treated with Pd2(dba)3 (0.030 g, 0.033 mmol) and Cy-JohnPhos (0.011 g, 0.033 mmol). The resulting reaction mixture was heated at 110C for 16 h then cooled to rt and poured into water (50 ml). The obtained mixture was extracted with EtOAc (3 x 20 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (2% MeOH in DCM) yielding tert-butyl l-(5-phenylthiazol-2-yl)octahydro-6H- pyrrolo[3,4-b]pyridine-6-carboxylate (0.163 g, 0.422 mmol). LCMS: Method C, 2.766 min, MS: ES+ 386.38. |
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