HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 59127148, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 6-chloropyridine-3-carboxylate | HCID 254249 | — |
| Reactant | 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide | HCID 53629632 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 59127148 | HCID 59127148 | 73.2% |
Reaction Steps
A solution of 3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (1.00 g, 2.47 mmol), methyl 6-chloronicotinate (0.450 g, 2.60 mmol), and cesium carbonate (1.204 g, 3.71 mmol) in acetonitrile (15 mL) was heated at 160° C. using microwave heating for 90 minutes. The acetonitrile was removed in vaccuo and the residual oil partitioned between water (50 mL) and ethyl acetate (75 mL). The ethyl acetate layer was separated, washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with 50% ethyl acetate in isohexane, to give the desired compound (0.977 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07642259B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-1a4223bf07cd44f48f31af47c4792106 |
| Source note | uspto-grants-2010_01 |