Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 11851868 | HCID 11851868 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67215739 | HCID 67215739 | — |
Reaction Steps
0.79 g (2.43 mmol) of cesium carbonate and then 0.05 ml (0.84 mmol) of methyl iodide are added to 0.22 g (0.76 mmol) of (4-amino-3-methoxyphenyl)(8-hydroxyimidazo[1,5-a]pyridin-3-yl)methanone obtained in example 147 in 5 ml of DMF. The reaction medium is stirred at ambient temperature for 4 hours. After addition of a saturated sodium hydrogencarbonate solution, the reaction medium is extracted with ethyl acetate. The organic phase obtained is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel, elution being carried out with dichloromethane. 0.2 g of an orange-yellow solid is collected. Melting point: 229° C.; 1H NMR (CDCl3): 3.86 (3H, s), 4.01 (3H, s), 5.80 (2H, m), 6.69 (1H, m), 6.69-6.72 (1H, m), 7.03-7.09 (1H, t), 7.78 (1H, s), 7.92 (1H, s), 8.24 (1H, m), 9.25-9.28 (1H, m)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08008321B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-49aa91abdf3d458c99839d4c21e3bfac |
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| Source note | uspto-grants-2011_08 |
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