Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-[(tert-Butoxycarbonyl)amino]cyclohex-1-en-1-yl trifluoromethanesulfonate | HCID 59832199 | — |
| Reactant | HCID 68753732 | HCID 68753732 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68752610 | HCID 68752610 | — |
Reaction Steps
N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxamide (1.692 g, 4.63 mmol), 4-(tert-butoxycarbonylamino)cyclohex-1-enyl trifluoromethanesulfonate (1.6 g, 4.63 mmol) and cesium carbonate (3.77 g, 11.58 mmol) were suspended in terahydrofuran (30 ml), methanol (5.00 ml) and water (15.00 ml). Nitrogen was bubbled throught the solution for 10 min when PdCl2(dppf)-dichloromethane adduct (0.189 g, 0.232 mmol) was added and the mixture was heated to 80° C. for 7 h. After dilution with ethyl acetate and brine, the separated aqueous layer was extracted several times with ethyl acetate and the combined organic layers were dried over magnesium sulfate, filtered and concentrated. Flash chromatography provided the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09302989B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-c62184a3dad34bc1b9102857b07f4c4b |
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| Source note | uspto-grants-2016_04 |
|---|