Methyl iodide → HCID 56645876, compound
Reaction equation
[C:1]([C:3]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]3[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15]([CH3:22])[N:14]=3)[CH2:9][CH2:8]2)[O:5][N:4]=1)#[CH:2].[CH2:23]([Li])CCC.CCCCCC.CI>C1COCC1>[CH3:22][C:15]1[N:14]=[C:13]([N:10]2[CH2:11][CH2:12][C:6]3([O:5][N:4]=[C:3]([C:1]#[C:2][CH3:23])[CH2:7]3)[CH2:8][CH2:9]2)[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Into a solution of Compound 11a (25 mg, 0.83 mmol) in THF (1.26 mL) kept under stirring at −78° C., Butyllithium in Hexane (2.5 M, 0.04 mL, 0.1 mmol) is added dropwise. After 30 min., methyl iodide (6.22 μL, 0.1 mmol) was added. The cold bath was removed and the orange solution was allowed to reach r.t. After overnight resting, it was quenched with a saturated aqueous NH4Cl sol., extracted with EtOAc, washed with H2O, dried on Na2SO4 and the solvent was evaporated to dryness in vacuo. The crude the crude was purified by automated flash liquid chromatography (Horizon®TM-Biotage) (Petroleum Ether-EtOAc gradient from 95:5 to 6:4) giving 6 mg of the title compound. Yield: 22.9%.
Workup
- customThe cold bath was removed
- customto reach r.t
- waitAfter overnight resting
- customit was quenched with a saturated aqueous NH4Cl sol.
- extractionextracted with EtOAc
- washwashed with H2O
- customdried on Na2SO4
- customthe solvent was evaporated to dryness in vacuo
- customThe crude the crude was purified by automated flash liquid chromatography (Horizon®TM-Biotage) (Petroleum Ether-EtOAc gradient from 95:5 to 6:4)
Sources & evidence
- ORD record
- ord-279dfa67b2ca448bad0442ee1a4483b3
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580962B2
Reaction notes
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