Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 71143555 | HCID 71143555 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71143669 | HCID 71143669 | 88% |
Reaction Steps
2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]-1-oxo-isoindoline-5-carbonitrile (111 mg, 0.1586 mmol) dissolved in a mixture of DCM (10 mL) and MeOH (5 mL) under N2. CoCl2 (41.18 mg, 0.3172 mmol) added and resulting green solution cooled in an ice bath. NaBH4 (60 mg, 1.586 mmol) added in one portion and the ice bath removed. After 2 h reaction re-cooled in an ice bath and water (˜5 mL) added. Mixture diluted with DCM (˜20 mL) and stirred vigorously for 20 mins. Layers separated and aqueous extracted with DCM. Aqueous phase basified by addition of sat NaHCO3 solution and extracted with DCM (×2). Combined organics dried and concentrated to give the title compound as a yellow solid 88% pure by UV (112 mg, 82%); MS (ES+) 704.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09309250B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-2338e061897649e091aa11e7ea86d9ae |
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| Source note | uspto-grants-2016_04 |
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