Methyl iodide → (6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[N:10][C:11]([Br:14])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[N:10][C:11]([Br:14])=[CH:12][CH:13]=1)[CH3:21])([CH3:4])([CH3:2])[CH3:3]Participants
5
Procedure
To a stirred solution of (6-bromo-2-nitro-pyridin-3-yl)-carbamic acid tert-butyl ester (6) (290 mg, 0.91 mmol) in DMF (10 mL), NaH (57 mg, 1.36 mmol, 57% dispersion in oil) was added at 0° C. After stirring for 15 minutes, methyl iodide (79 μL, 1.27 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction mixture was then quenched with saturated ammonium chloride solution (15 mL) and extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography using 20% ethyl acetate in hexane to give compound (7) (268 mg) as a pale yellow solid.
Workup
- stirringthe reaction mixture was stirred for 1 hour
- customThe reaction mixture was then quenched with saturated ammonium chloride solution (15 mL)
- extractionextracted with ethyl acetate (2×40 mL)
- washThe combined organic extracts were washed with water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography
Sources & evidence
- ORD record
- ord-60e3453f36924b73a8596ffa2801bfda
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309267B2
Reaction notes
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