Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 1-bromo-3-iodo-5-(trifluoromethoxy)benzene | HCID 2761169 | — |
| Reactant | (6-Methylpyridin-3-yl)methanamine | HCID 12214337 | — |
| Catalyst | Molybdenum carbonyl (Mo(CO)6) | HCID 98885 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | HCID 58188114 | HCID 58188114 | — |
Reaction Steps
A 5 mL microwave vial was charged with 1-bromo-3-iodo-5-(trifluoromethoxy)benzene (98 mg, 0.27 mmol), (6-methylpyridin-3-yl)methanamine (50 mg, 0.41 mmol), molybdenum hexacarbonyl (160 mg, 0.61 mmol), palladium acetate (8 mg, 0.036 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (120 mg, 0.79 mmol), and 1,4-dioxane (2 mL). The vial was sealed under nitrogen and the reaction was subjected to microwave irradiation at 120° C. for 20 minutes. After cooling, the mixture was purified via flash chromatography to afford the desired product as a white solid. LC-MS: 391.2 [M+1]+; 1H NMR (CDCl3, 400 MHz): 8.43 (d, J=2.1 Hz, 1H), 7.85 (t, J=1.5 Hz, 1H), 7.63-7.61 (m, 2H), 7.52 (s, 1H), 7.16 (d, J=8.0 Hz, 1H), 6.74 (br, 1H), 4.60 (d, J=5.8 Hz, 2H), 2.55 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946439B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-29147acebbec4ad09de7fa11e7cdab62 |
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| Source note | uspto-grants-2015_02 |
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