Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 4642098 | — |
| Reactant | HCID 86692546 | HCID 86692546 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86692545 | HCID 86692545 | 94.9% |
Reaction Steps
To N-(6-bromopyridin-3-yl)-5-methyl-1-[5-(tri fluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (3.0 g), cesium carbonate (6.4 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloridedichloromethane complex (287 mg), and N-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (2.28 g) were added 1,4-dioxane (26 ml) and water (7 ml), and stirred at 110° C. for 6.5 hours. To the reaction solution was added water, and the obtained solid was washed with a mixed solution of n-hexane and ethyl acetate to give N-[6-(1-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (3.53 g) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09150555B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-81126a5beb404743b6809da65f332baf |
|---|
| Source note | uspto-grants-2015_10 |
|---|
