Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Simtuzumab | HCID 17750227 | — |
| Reactant | HCID 53212388 | HCID 53212388 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethylene Glycol Monomethyl Ether | HCID 8134 | — |
| Product | HCID 67974881 | HCID 67974881 | 68.6% |
Reaction Steps
A mixture of 2-chloro-6-methoxy-3-(trifluoromethyl)quinoxaline (Intermediate 11, 150 mg, 0.571 mmol), 4-carboxy-2-chlorophenylboronic acid (115 mg, 0.571 mmol), K2CO3 (160 mg, 1.14 mmol) and Pd(dppf)Cl2 (50 mg, 0.0612 mmol) in diethylene glycol monomethyl ether (2 mL) and water (0.6 mL) was stirred at 120° C. under N2 atmosphere for 2 hours. The resulting mixture was cooled to room temperature and diluted with water (50 mL), acidified with aqueous HCl (2M) until pH=5, extracted with EtOAc (50 mL×3), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=1/1) to give the product (150 mg, yield 68%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09364481B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-936fc3de6bcf4ddcaaf276316438219e |
|---|
| Source note | uspto-grants-2016_06 |
|---|
