Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Trifluoroacetate | HCID 517019 | — |
| Reactant | HCID 57933083 | HCID 57933083 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Dimethylformamide toluene | HCID 21735183 | — |
| Product | HCID 57933053 | HCID 57933053 | 38.3% |
Reaction Steps
170 mg of 3-(4-Bromo-2-morpholin-4-yl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.37 mmol) and 100 mg of sodium trifluoroacetate (0.74 mmol) are dissolved in 3 ml of DMF/toluene=2/1. N2 gas is bubbled into the mixture for 20 min and 141 mg of CuI (0.74 mmol) is added. The vial is sealed and heated in the microwave at 210° C. for 30 min. The reaction mixture is applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1 and CH3CN:CH2Cl2:Hexane=5:45:50) to give 64.3 mg of the title compound. Yield 38%. mass spectrum (m/e): 454 (M+1). 1H NMR (CDCl3): δ 6.72 (s, 1H), 3.88 (m, 4H), 3.60 (m, 4H), 3.32 (m, 1H), 2.54 (s, 3H), 2.47 (s, 3H), 1.85 (m, 4H), 0.89 (t, J=7.0 Hz, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07612067B2 |
|---|
| Source dataset | uspto-grants-2009_11 |
|---|
| ORD ID | ord-06bd896497974d26b890963f8b535c15 |
|---|
| Source note | uspto-grants-2009_11 |
|---|
