Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate | HCID 16217654 | — |
| Reactant | HCID 86722865 | HCID 86722865 | — |
| 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 136348394 | HCID 136348394 | 105.4% |
Reaction Steps
A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-b]pyridine (60 mg, 0.1 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (40. mg, 0.13 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (7 mg, 0.009 mmol), and potassium phosphate (48 mg, 0.22 mmol) in 1,4-dioxane (0.5 mL) and water (0.07 mL) in a reaction vial was degassed and sealed. It was stirred at 85° C. overnight. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (50 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09266892B2 |
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| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-09bf384f28384225a3cd185069c2a2c3 |
|---|
| Source note | uspto-grants-2016_02 |
|---|
