Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium | HCID 223 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Sodium ethanethiol | HCID 45051917 | — |
| Reactant | HCID 117974134 | HCID 117974134 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 117974188 | HCID 117974188 | 43.9% |
Reaction Steps
A mixture of 0.72 g of 2-(2-bromothiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine, 0.25 g of ethyl mercaptan sodium salt (80%), 0.08 g of copper iodide and 4 ml of N-methylpyrrolidinone was stirred at 70° C. for 4 hours. Water and aqueous ammonium (28%) were poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.30 g of 2-(2-ethylthiothiophen-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound of Present Invention (13)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09120792B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-f74e72c736fe43289fe86d2c8a838b3d |
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| Source note | uspto-grants-2015_09 |
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