JBG43-1
JBG43-1 Synthesis of ethyl 6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate
Experiment Status: Completed
| Name | MW | mmol | Equiv. | quantity (g) | Volum (mL) | Supplier | Risk Numbers |
| 2-amino-4-bromo-3-(trifluoromethyl)pyridine JBG28-1-1 | 241 | 6.224066 | 1 | 1.5 | JBG28-1 | unknown, treat as a toixc | |
| Ethyl bromopiruvate | 195.01 | 12.44813 | 2 | 2.42751 | 1.562104 | Aldrich | R36/37/38 H315 H319 H335 |
| DMF | 12 |
R61, R20/21, R36
|
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| Product: 6-bromo-8-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate JBG43-1-1 | 337.093 | 6.224066 | 1 | 2.09808908 | unknown, treat as a toixc |
Procedure
To a solution of 2-amino-4-bromo-3-(trifluoromethyl)pyridine (1.50 g, 6.22 mmol, 1 equiv.) in DMF (12 mL) was added ethyl bromopyruvate (1.56 mL, 12.45 mmol, 2 equiv.) and the mixture was heated at 50 ยบC for 24 h.
Time: 12.30
Appearance: yellow solution, after few minutes became orange and then brown
After cooling down the solvent was removed to half volume and diluted with EtOAc (50 mL) and washed with water (3 x 50 mL) and brine (3 x 50 mL). The organic phase was dried over MgSO4, filtered and evaporated to obtain the crude as brown oil. (3.10 g)
The crude was dissolved in EtOAc (3 mL) and dripped slowly into Cyclohexane (45 mL) and stirred overnight. A beige suspension started to precipitated. The suspension was filtered and washed with cyclohexane to get the desired product JBG43-1-1 as a light brown solid (1.59 g, 4.70 mmol, 76%)
Vial weight : 58.5627
References
Piperidinyl cyclic amido antiviral agents WO 2010091411 A1
CONCLUSIONS
The desired compound JBG43-1-1 was successfully synthesised in 76 % yield and it was used in JBG45-1
Note
OSTBS number : OSTBS29