Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 6-((methylsulfonyloxy)methyl)picolinate | HCID 54451634 | — |
| Reactant | 6-(4-Hydroxy-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile | HCID 136011085 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 67144610 | HCID 67144610 | 78.8% |
Reaction Steps
A mixture of methyl 6-((methylsulfonyloxy)methyl)picolinate (733 mg), 6-(4-hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (950 mg), sodium iodide (44 mg) and potassium carbonate (830 mg) in acetonitrile (20 ml) was heated at 80° C. for 14 hours. After cooling to room temperature, water (30 ml) was added, the white precipitate was collected by filtration and washed with cold methanol (20 ml) to give methyl 6-((4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)methyl)picolinate (1.1 g). 1H NMR (DMSO) δ: 8.81 (s, 1H), 8.71 (s, 1H), 8.53 (m, 2H), 8.20 (m, 1H), 8.11 (m, 1H), 7.83 (d, 1H), 7.63 (d, 1H), 5.60 (s, 2H), 4.06 (s, 3H), 3.98 (s, 3H). MS m/z 468 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08026236B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-eccf180b5bb34f9e97179b47bbe6c3c1 |
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| Source note | uspto-grants-2011_09 |
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