Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Guaiacol | HCID 460 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tert-butyl 3-(3-chloropyrazin-2-yl)azetidine-1-carboxylate | HCID 59351411 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 58547489 | HCID 58547489 | 61% |
Reaction Steps
A mixture of 3-(3-chloro-pyrazin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (7) (100 mg, 0.37 mmol), 2-methoxy-phenol (47 mg, 0.37 mmol) and Cs2CO3 (242 mg, 0.74 mmol) in DMSO (10 mL) was stirred at 90° C. overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude compound, which was purified by column chromatography to afford pure product (13) (80 mg, 0.22 mmol, yield 61%) as solid. ESI-MS (M+1): 358 calc. for C19H23N3O4 357.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957073B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-4cd0ddfdcd8f4eb9a624291b565e7894 |
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| Source note | uspto-grants-2015_02 |
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