HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 68093911, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methylboronic Acid | HCID 139377 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | HCID 66728118 | HCID 66728118 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | HCID 68093911 | HCID 68093911 | 20.1% |
Reaction Steps
A mixture of 3-[4-(5-chloropyridin-2-yloxy)phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine (58 mg), methylboronic acid (59.4 mg), Pd(dppf)2Cl2 (18 mg) and Cs2CO3 (766 mg) in DME/H2O (4 mL, 3/1) was exposed to microwave irradiation at 140° C. for 1 h, and then Pd(OAc)2 (3.7 mg), Xphos (15.7 mg) and Cs2CO3 (107 mg) were added. The mixture was exposed to microwave irradiation at 140° C. for 1 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC (H2O in CH3CN containing 10 mM NH4HCO3). Crystallization from AcOEt/hexane gave title compound (11 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029536B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-b9bac3a8dc234404a187e40c4cd068b5 |
| Source note | uspto-grants-2015_05 |