Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | HCID 14942816 | HCID 14942816 | — |
| Reactant | 8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine | HCID 57752681 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57932903 | HCID 57932903 | 77.1% |
Reaction Steps
3.00 g of 8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (8.74 mmol), 4.32 g of 4-methyl-2H-thiazole (43.6 mmol), 453 mg of triphenylphosphine (1.73 mmol) and 5.85 g of cesium carbonate (18.0 mmol) are placed into the sealed tube with 20 ml of DMF and N2 gas is bubbled in for 40 min. 39 mg of Pd2 dba3 (0.43 mmol) is added and the tube is sealed and heated at 130° C. overnight. The cooled reaction mixture is filtered and applied onto silica-gel column (Hexane→Hexane:AcOEt=3:1) to give 2.12 g of the title compound (77%). 1H-NMR (DMSO-d6) δ 9.215 (s, 1H); 6.993 (s, 1H); 3.079 (m, 1H); 2.480 (s, 3H); 2.439 (s, 3H); 2.302 (s, 3H); 1.824-1.751 (m, 4H); 0.780-0.743 (m, 6H) ppm. MS, ES+=315.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07612067B2 |
|---|
| Source dataset | uspto-grants-2009_11 |
|---|
| ORD ID | ord-1c2c5cc4bd6a422a85854b4869cc4e2f |
|---|
| Source note | uspto-grants-2009_11 |
|---|