HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → HCID 178478381, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Chlorophenylboronic acid | HCID 2734322 | — |
| Reactant | Potassium phenoxide | HCID 23670670 | — |
| Reactant | HCID 178478383 | HCID 178478383 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178478381 | HCID 178478381 | 63% |
Reaction Steps
To (2-Chloro-6-iodo-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (100 mg, 0.243 mmol) and 2-chlorophenyl boronic acid (57 mg, 0.364 mmol) in DMSO (5 mL, purged with Ar) was added 1.5M potassium phenolate solution (648 μL, 0.97 mmol) and 1,1′bis(diphenylphosphino)ferrocene palladium chloride, complex with dichloromethane (27 mg) and the solution was heated to 60 C in a sealed tube. After 1 hr, solution was poured into sat. NaHCO3 resulting in a yellow solid that was colleted by filtration. Flash chromatography (1-4% methanol in dichloromethane) to give: 73 mg (63% yield). LCMS m/e: 396.2 (M+H), 394.2 (M-H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07842712B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-eba73d1f78184cff80cccd1cc6e7c417 |
| Source note | uspto-grants-2010_11 |