Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 178522942 | HCID 178522942 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 10095695 | HCID 10095695 | 92% |
Reaction Steps
To a solution of N-(4-chlorobenzyl)-4-hydroxy-2-iodothieno-[2,3-b]pyridine-5-carboxamide (Example No. 2) (2.00 g) in DMF (14 mL) are added K2CO3 (1.76 g) and iodomethane (0.79 mL). The reaction is heated to 90° C. and stirred for 18 h. The reaction mixture is concentrated in vacuo. The resulting residue is partitioned between H2O (100 mL) and CH2Cl2 (200 mL). The aqueous layer is extracted with CH2Cl2 (3×150 mL). The combined organic layers are dried with MgSO4, filtered, and concentrated in vacuo. The resulting off-white solid is recrystallized from ethanol to yield 1.78 g (92%) of the title compound as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06239142B1 |
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| Source dataset | uspto-grants-2001_05 |
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| ORD ID | ord-0cdb5584570643a7b7198a4452ad164a |
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| Source note | uspto-grants-2001_05 |
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