Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Phenethyl bromide | HCID 7666 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 59563693 | HCID 59563693 | — |
| Product | HCID 66599827 | HCID 66599827 | — |
Reaction Steps
To tert-butyl 2-(4-hydroxyphenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E249) in DMF cooled to −35° C. was added NaH and the solution was stirred at −40° C. for 30 min. Then, 2-bromoethylbenzene was added and the solution was warmed and stirred at room temperature for 2 h. The solution was poured into NaHCO3(sat)/EtOAc and further extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 3-4% MeOH/CH2Cl2) gave pure tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(phenethoxyphenyl)propylcarbamate (E289).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394826B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-bbb50252f9f245d89813751d0261278e |
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| Source note | uspto-grants-2013_03 |
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