Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromo-2-isonicotinoylthiophene-3-carboxylic acid | HCID 71743608 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 89539133 | HCID 89539133 | 25.1% |
Reaction Steps
A mixture of ethyl iodide (3.78 mL, 48.06 mmol), Cs2CO3 (15.66 g, 48.06 mmol) and 4-bromo-2-isonicotinoylthiophene-3-carboxylic acid (5 g, 16.02 mmol) in CH3CN (150 mL) was stirred at room temperature for about 12 h in a 250 mL round-bottomed flask. After completion of the reaction, the solvent was removed under reduced pressure. The reaction mixture was diluted with water and the aqueous layer was back extracted with ethyl acetate (3×100 mL). The combined organic layers were dried with Na2SO4, filtered and concentrated to afford a yellow solution. The resulting mixture was deposited onto silica gel, loaded onto a silica gel column and eluted with 5:1 PE/EtOAc to give the title compound (1.37 g, 25% yield). LC-MS (Method A): m/z 340 (M+H)+, Rt: 1.07 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09200005B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-773300a27da944a59b30b2ee1c2f903c |
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| Source note | uspto-grants-2015_12 |
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