Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| 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 62909797 | HCID 62909797 | — |
| Catalyst | Hydrochloric Acid | HCID 313 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 44539625 | HCID 44539625 | 36.1% |
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 (55 mg), N-(5-bromo-2-chlorophenyl)methanesulfonamide (39 mg), sodium carbonate (48 mg) and Pd(dppf)Cl2 (8.3 mg) were weighed to a microwave vial. 1,4-Dioxane (0.5 ml) and water (0.5 ml) were added and the reaction was heated under microwave irradiation at 140° C. for 20 min. The reaction was passed through a 1 g silica SPE cartridge preconditioned with MeOH, washing with MeOH, the evaporated to dryness. The residue was dissolved in DMSO:MeOH (1:1, v/v, 1 ml) and purified by MDAP (method E). The residue obtained was dissolved in MeOH and a couple of drops of 2M HCl (aq) were added. The reaction was stirred for 2 h and evaporated to dryness to give the title compound (19 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08163743B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-2c402367a3084649977965b6b59fa192 |
|---|
| Source note | uspto-grants-2012_04 |
|---|
