Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| 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 | (4-Bromo-1H-pyrazol-1-yl)acetic acid | HCID 17024755 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Potassium Carbonate | HCID 11430 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 89726251 | HCID 89726251 | 88% |
Reaction Steps
A mixture of 2-(4-bromo-1H-pyrazol-1-yl)acetic acid (867 mg), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.2 g) and Pd(PPh3)4 (232 mg) in dioxane (15 mL) and sat. K2CO3 (7.5 mL) was heated at 100° C. overnight. After cooling down, EA was added and the mixture was washed with water and brine. The combined aq. layers were acidified to pH=2 with NaHSO4 and extracted with EA. The org. layers from the second extraction were dried (MgSO4), filtered off and evaporated in vacuo to afford 1.05 g of brown resin that was used without purification. LC-MS (B): tR=0.72 min; [M+H]+: 308.26.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266876B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-6a98f47c8d31451ba19bca4b0b4ae57c |
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| Source note | uspto-grants-2016_02 |
|---|