Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 44540317 | HCID 44540317 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethyl sulfoxide methanol | HCID 22036561 | — |
| Product | HCID 44539731 | HCID 44539731 | 22.8% |
Reaction Steps
5-Bromo-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (35 mg, 0.08 mmol) and morpholine (1 ml, 11.5 mmol) were placed in a microwave vial. Pd2dba3 (4 mg, 0.004 mmol), BINAP (5 mg, 0.008 mmol) and cesium carbonate (40 mg, 0.12 mmol) were added and the mixture was heated at 150° C. for 75 mins under microwave irradiation. The reaction mixture was concentrated in vacuo to give a crude residue that was suspended in 1:1 DMSO/MeOH (1 ml) and filtered to give an orange solution that was purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1 g aminopropyl column, eluted with MeOH and the solvent removed under a stream of nitrogen to give the title compound (8 mg) as a pale orange solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765743B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-a135e9b44c7749daa90fd7a9e61f4d87 |
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| Source note | uspto-grants-2014_07 |
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