Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2,2-Dimethylpyrrolidine | HCID 414773 | — |
| Reactant | 8-Bromo-6-chloroimidazo(1,2-b)pyridazine | HCID 46835269 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86682700 | HCID 86682700 | 55.8% |
Reaction Steps
To a solution of 2,2-dimethylpyrrolidine (0.248 g, 2.5 mmol) in DMF (8 mL) was added NaH (0.060 g, 60% dispersion in mineral oil, 2.5 mmol) and stirred for 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.233 g, 1 mmol) under N2. The mixture was stirred at room temperature for 16 h. Then it was partitioned between 15 mL of saturated NH4Cl solution and 15 mL of ether. The organic layer was washed with water (10 mL×3) and saturated NaCl solution (10 mL×3), dried over NaSO4, concentrated in vacuo, and purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 6-chloro-8-(2,2-dimethylpyrrolidin-1-yl)imidazo[1,2-b]pyridazine (0.140 g, 22%) as a light brown solid. LC-MS: [M+H]+, 251.1, tR=1.698 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09169259B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-525e48a000a748dc8e0cdd3746179395 |
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| Source note | uspto-grants-2015_10 |
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