Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 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 | (5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine | HCID 86664780 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67494206 | HCID 67494206 | 96,860.5% |
Reaction Steps
To a 40 mL scintillation vial was charged 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)-ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.86 mmol, 480 mg), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.30 mmol, 400 mg), K3PO4 (2.60 mmol, 550 mg), and PdCl2(dppf).CH2Cl2 (0.086 mmol, 70 mg). To this reaction mixture was added a 9:1 solution of 1,4-dioxane:H2O (10 mL). The vial was flushed with argon, sealed with Teflon tape, and stirred at 100° C. 18 hours. After 18 hours, the reaction was concentrated in vacuo and the residue purified via silica gel chromatography to yield tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (586 mg, 833 mmol, 97% yield) as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08591943B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-0e04b33a54ad4d3fb21faeabfb894a57 |
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| Source note | uspto-grants-2013_11 |
|---|
