Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Cyclopropyl-5-(tributylstannyl)isothiazole | HCID 71143869 | — |
| Reactant | tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate | HCID 86654748 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 71144066 | HCID 71144066 | — |
Reaction Steps
A solution of tert-butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (50 mg, 0.100 mmol), 3-cyclopropyl-5-(tributylstannyl)isothiazole (62.0 mg, 0.150 mmol) and tetrakis(triphenylphosphine)palladium(0) (34.6 mg, 0.030 mmol) in toluene (10 mL) was heated to 120° C. for 45 minutes via microwave irradiation. The reaction mixture was poured into water and was extracted with EtOAc. The extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (Flash 60 column) eluting with hexane/EtOAc (1:1) to give the title compound as a yellow solid, which was used without further purification (58.9 mg, 100%). ESI-MS m/z [M+H]+ calc'd for C28H36FN5O6S, 590. found, 590.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09056873B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-71a01f1e08e8494a8172e06a9c6f957e |
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| Source note | uspto-grants-2015_06 |
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