HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → methyl 4-bromo-3-(methyloxy)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Reactant | methyl 4-bromo-3-hydroxy-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate | HCID 57826681 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | methyl 4-bromo-3-(methyloxy)-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate | HCID 57826414 | 74% |
Reaction Steps
To a solution of methyl 4-bromo-3-hydroxy-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (175 mg, 0.554 mmol), MeOH (26 μL, 0.609 mmol), PPh3 (189 mg, 0.720 mmol) in THF (6 mL) at 25° C. was added DEAD (113 μL, 0.720 mmol) in one portion. After 30 min, the reaction was concentrated and purified via column chromatography (silica, 20% EtOAc in hexanes) affording the title compound (135 mg, 74%) as a white solid: LC-MS (ES) m/z=332 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08273782B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-e1ed1ce7981849f6999a65017ddc76df |
| Source note | uspto-grants-2012_09 |