Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Potassium cyclopropyltrifluoroborate | HCID 23697338 | — |
| Reactant | HCID 59494314 | HCID 59494314 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 59494829 | HCID 59494829 | 41.7% |
Reaction Steps
Tetrakis(triphenylphosphine)palladium(0) (20 mg) was added to a solution of tert-butyl {[3-bromo-1-(3-methoxypropyl)-1H-indazol-6-yl]methyl}cyclopropylcarbamate (150 mg), potassium cyclopropyltrifluoroborate (73 mg) and potassium phosphate (254 mg) in toluene (3 ml)-water (1 ml) under argon atmosphere and the mixture was stirred at 100° C. for 24 hours. Potassium cyclopropyltrifluoroborate (24 mg), potassium phosphate (73 mg) and tetrakis(triphenylphosphine)palladium(0) (20 mg) were added to the reaction mixture and it was stirred further at 100° C. for 24 hours. Water was added to the reaction mixture under ice-cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane to n-hexane/ethyl acetate=2/1) to give tert-butyl cyclopropyl{[3-cyclopropyl-1-(3-methoxypropyl)-1H-indazol-6-yl]methyl}carbamate (57 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08975252B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-142b12ceac7f4ea9b874b78f5eb33081 |
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| Source note | uspto-grants-2015_03 |
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