HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → HCID 89497971, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 1-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2734771 | — |
| Reactant | 1,1-Dimethylethyl 6-(8-((2-benzothiazolylamino)carbonyl)-3,4-dihydro-2(1H)-isoquinolinyl)-3-bromo-2-pyridinecarboxylate | HCID 59447615 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 89497971 | HCID 89497971 | — |
Reaction Steps
A mixture of EXAMPLE 1D (0.113 g), 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.063 g), tetrakis(triphenylphosphine)palladium(0) (0.023 g) and CsF (0.091 g) in 1,2-dimethoxyethane (2 mL) and methanol (1 mL) was heated at 120° C. for 30 minutes under microwave heating conditions. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 35% ethyl acetate in hexanes to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08940737B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-95ccd19300be4e2485229fa4f38526bd |
| Source note | uspto-grants-2015_01 |