HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 59773106, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol | HCID 2734624 | — |
| Reactant | HCID 59773105 | HCID 59773105 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59773106 | HCID 59773106 | 61.1% |
Reaction Steps
A solution of {4-((5-bromo-2-methyl-furan-3-carbonyl)-amino]-phenyl}-acetic acid ethyl ester (3 g, 8.19 mmoles) (15), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (1.8 g, 8.19 mmoles), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (300 mg, 10%) and 2M aqueous cesium carbonate (15 ml, 15 mmoles) in N,N-dimethylformamide (35 ml) was heated in a microwave reactor at 100° C. for 15 minutes. The solvent was evaporated, and the residue was purified by flash chromatography (gradient elution with 100% cyclohexane to 100% ethyl acetate) to afford (4-{[5-(4-hydroxy-phenyl)-2-methyl-furan-3-carbonyl]-amino}-phenyl)-acetic acid ethyl ester (16) (1.9 g). LC/MS System A; Rt=3.54 mins, m/z (ES+)=380 (M+H for C22H21NO5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07569602B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-a7537b1967ed44b589b75992234c098e |
| Source note | uspto-grants-2009_08 |