Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-(Bromomethyl)-2-chloro-4-fluorobenzene | HCID 2725062 | — |
| Reactant | HCID 178505585 | HCID 178505585 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Lxr-623 | HCID 16734800 | 42.2% |
Reaction Steps
To a solution of 3-(4-fluoro-phenyl)-7-trifluoromethyl-1H-indazole (6.43 g, 23 mmol) in 20 mL DMF was added 2-chloro-4-fluoro benzyl bromide (7.0 g, 31 mmol). The reaction mixture was heated overnight at 120° C. After cooling to room temperature, ethyl acetate was added and the solution was washed three times with brine. The organic layer was dried over NaSO4 and concentrated. Flash chromatography (hexane/CH2Cl2, 1:1, as eluent) afforded 4.1 g of pure product. Three grams (3 g) of product were recrystallized from 10 mL of isopropanol to recover 1.98 g of crystalline product, mp 78° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07592363B2 |
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| Source dataset | uspto-grants-2009_09 |
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| ORD ID | ord-297433edd05f4d8889aaec15a6c4cb48 |
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| Source note | uspto-grants-2009_09 |
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