Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1H-Pyrazole-5-boronic acid | HCID 11251979 | — |
| Reactant | HCID 59333310 | HCID 59333310 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 25120170 | HCID 25120170 | 40.2% |
Reaction Steps
A solution of 3-({1-iodo-7-[2-(trifluoromethyl)phenyl]imidazo[1,2-a]quinoxalin-4-yl}amino)propan-1-ol (42 mg; 0.082 mmol; 1 eq), 1,1′bis(diphenylphosphino) ferrocene)palladium dichloride. dichloromethane complex (20.1 mg; 0.025 mmol; 0.3 eq), 1H-pyrazole-5-boronic acid (18.3 mg; 0.164 mmol; 2 eq) and sodium carbonate (26 mg; 0.246 mmol; 3 eq) in anhydrous dimethylformamide (0.37 ml) is stirred under argon at 100° C. for 4 h. Partition (aqueous sodium hydrogenocarbonate/ethyl acetate), filtration over Celite, extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5) affords the title product (15 mg; 0.033 mmol; 39%) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08513250B2 |
|---|
| Source dataset | uspto-grants-2013_08 |
|---|
| ORD ID | ord-5d2a102d4e7c41f689e85e169d999d95 |
|---|
| Source note | uspto-grants-2013_08 |
|---|