Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | 8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine | HCID 57752681 | — |
| Reactant | 3-Bromo-5-chlorothieno[3,2-b]pyridine | HCID 71464339 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86621041 | HCID 86621041 | 3% |
| Product | HCID 86621042 | HCID 86621042 | 2% |
Reaction Steps
248 g of 3-Bromo-5-chloro-thieno[3,2-b]pyridine (1.0 mol) is dissolved in 2.0 l of dry THF and cooled to −78° C. 0.4 l of n-BuLi 2.5M in hexane (1.0 mol) is added slowly and stirred at −78° C. for 15 in. 2.0 l of 0.5M ZnCl2 in THF (1.0 mol) is added and stirred at room temperature for 20 in. 343 g of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.0 mol) and 37 g of PdCl2(dppf) (0.05 mol) are added and the reaction vial is capped with a Teflon cap. The vial is heated at 80° C. overnight. The reaction mixture is filtered and applied onto a silica-gel chromatography column (1st column; hexane AcOEt=10:1, 2nd column; CH3CN:CH2Cl2:Hexane=1:5:4) to give 16 mg of 3-(3-bromo-5-chloro-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (3%) and 9 mg of 3-(5-chloro-thieno[3,2-b]pyridin-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (2%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07557103B2 |
|---|
| Source dataset | uspto-grants-2009_07 |
|---|
| ORD ID | ord-1baf341a6e8f4cabaadffd55d6874970 |
|---|
| Source note | uspto-grants-2009_07 |
|---|
