Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide | HCID 58255833 | — |
| Reactant | HCID 178527451 | HCID 178527451 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 178433039 | HCID 178433039 | 41% |
Reaction Steps
2-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide (27.5 mg) was dissolved in 1,4-dioxane (0.5 ml) and N-(5-bromo-2-hydroxy-3-pyridinyl)cyclopropanesulfonamide (40 mg) was added. Sodium carbonate (48 mg) and Pd(dppf)Cl2 (8.3 mg) were weighed before further 1,4-dioxane (0.5 ml) and water (1 ml) were added. The reaction was heated under microwave irradiation at 140° C. for 20 min. The reaction was added to a silica SPE cartridge that was eluted with MeOH. The MeOH was evaporated to dryness and the residue was dissolved in DMSO:MeOH (1.6 ml, 1:1, v/v) and purified by MDAP (method F) to give the title compound (11 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08163743B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-d8f01f85edaa47559cea1dc8d0db4cb2 |
|---|
| Source note | uspto-grants-2012_04 |
|---|
