Methyl iodide → HCID 68062851, compound
Reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[Br:13][C:14]1[C:15]2[CH:34]=[CH:33][CH:32]=[CH:31][C:16]=2[C:17]2[CH2:18][N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:20](=[O:23])[C:21]=2[CH:22]=1.IC.[Cl-].[NH4+]>O1CCCC1>[Br:13][C:14]1[C:15]2[CH:34]=[CH:33][CH:32]=[CH:31][C:16]=2[C:17]2[CH:18]([CH3:1])[N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:20](=[O:23])[C:21]=2[CH:22]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of diisopropylamine (0.30 mL, 2.1 mmol) in 1 mL of tetrahydrofuran cooled to 0° C. was added n-butyllithium (2.5 M tetrahydrofuran solution, 0.93 mL, 2.3 mmol) dropwise. After 30 min, the mixture was added to a −78° C. solution of 5-bromo-2-(2-fluorophenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one (0.150 g, 0.421 mmol) in 2 mL of tetrahydrofuran. After stirring for 30 min at −78° C., iodomethane (0.026 mL, 0.42 mmol) was added dropwise and after an additional 1 hr, the mixture was warmed to ambient temperature, treated with saturated aqueous ammonium chloride, and extracted 2× with ethyl acetate. The combined organic extracts were washed with water and brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the 5-bromo-2-(2-fluorophenyl)-1-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one that gave a proton NMR spectra consistent with theory.
Workup
- temperaturethe mixture was warmed to ambient temperature
- extractionextracted 2× with ethyl acetate
- washThe combined organic extracts were washed with water and brine
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified via preparative reverse phase HPLC
Sources & evidence
- ORD record
- ord-e0e959fdb6334db184858b7c58674ece
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697690B2
Reaction notes
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