Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | HCID 67777605 | HCID 67777605 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67777577 | HCID 67777577 | — |
Reaction Steps
To a solution of 6-(cyclopropylmethoxy)-2-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)-2H-indazole (218 mg) in THF (5 mL) was added dropwise a THF solution (1.11 M, 0.59 mL) of lithium diisopropylamide at −78° C. under an argon atmosphere, and the mixture was stirred for 30 min. To the reaction mixture was added methyl iodide (142 mg) at −78° C., and the mixture was stirred for 1.5 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (159 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08729102B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-e1f463331c2f47c09b48641ce695978b |
|---|
| Source note | uspto-grants-2014_05 |
|---|