Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Pentyne, 4,4-dimethyl- | HCID 518760 | — |
| Reactant | HCID 24808242 | HCID 24808242 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59264647 | HCID 59264647 | 80% |
Reaction Steps
To a suspension of 5-(5-bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (500 mg, 1.09 mmol), PdCl2(PPh3)2 (23 mg, 0.03 mmol), and CuI (4 mg, 0.01 mmol) in THF (10 mL) was added 4,4-dimethylpent-1-yne (176 mg, 1.30 mmol) and 0.5 M aqueous solution of 2-ethanolamine (3 mL). The resulting mixture was heated at 60° C. for 6 h. After cooled to room temperature, the reaction mixture was poured into water and diethyl ether (H2O/ether=1:1 (v/v), 20 mL). The aqueous layer was extracted with diethyl ether and the combined organic layers were concentrated to give a crude oil, which was purified by flash column chromatography with n-hexane/ethyl acetate (5:1) to afford the desired product (402 mg, 80%) as a light solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07705024B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-1578de0028d142f9b15232a9571485af |
|---|
| Source note | uspto-grants-2010_04 |
|---|
