Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | HCID 66584499 | HCID 66584499 | — |
| Reactant | 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine | HCID 77231218 | — |
| 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 86686735 | HCID 86686735 | — |
Reaction Steps
6-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (996.4 mg, 3.65 mmol), K3PO4 (1933.6 mg, 9.12 mmol), and PdCl2(dppf).CH2Cl2 (248 mg, 0.30 mmol) was added to a solution of 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (1684.3 mg, 3.04 mmol) in dioxane (18 mL) and H2O (3 mL). The resulting mixture was stirred at 80° C. under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded 5-chloro-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine: LCMS tR=3.34 Min (5 min run, UV254nm), Mass calculated for, M+573.2, observed LC/MS m/z 574.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08927562B2 |
|---|
| Source dataset | uspto-grants-2015_01 |
|---|
| ORD ID | ord-caeb2013bc524637a0eff53fe642d89e |
|---|
| Source note | uspto-grants-2015_01 |
|---|
