Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl (2S)-but-3-yn-2-ylcarbamate | HCID 10986677 | — |
| Reactant | HCID 86731236 | HCID 86731236 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86731235 | HCID 86731235 | 13.1% |
Reaction Steps
To a solution of 6-chloro-2-(4-(cyclopropylmethoxy)phenyl) [1,3]oxazolo[4,5-c]pyridine (700 mg), tert-butyl (2S)-but-3-yn-2-ylcarbamate (1.13 g) and triethylamine (0.649 g) in DMF (10 mL) were added bistriphenylphosphinedichloropalladium(II) (163 mg) and copper(I) iodide (88.7 mg), and the mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subjected to silica gel column chromatography (NH, ethyl acetate). The solvent was evaporated under reduced pressure, and the obtained solid was washed with ethyl acetate to give the title compound (132 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133129B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-beb092f8a1e8402e8755fb1ae1d3b1f2 |
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| Source note | uspto-grants-2015_09 |
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