Methyl iodide → (5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([N+:15]([O-:17])=[O:16])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I.[NH4+].[Cl-]>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([N+:15]([O-:17])=[O:16])[N:9]=1)[CH3:21])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (5-bromo-6-nitro-pyridin-2-yl)-carbamic acid tert-butyl ester (11) (800 mg, 2.52 mmol) in dry DMF (15 mL), NaH (60% dispersion in mineral oil, 191 mg, 4.53 mmol) was added at 0° C. The resulting mixture was stirred for 30 minutes at 0° C. and methyl iodide (0.23 mL, 3.68 mmol) was then added. After stirring the reaction mixture for 30 minutes at 10° C., saturated aqueous NH4Cl (15 mL) was added. The reaction mixture was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with water, brine, dried over MgSO4 (anhydrous) and concentrated under reduced pressure. The crude product was purified by Biotage using 10% ethyl acetate in hexane to afford (5-bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester 12 (789 mg).
Workup
- stirringAfter stirring the reaction mixture for 30 minutes at 10° C.
- extractionThe reaction mixture was extracted with ethyl acetate (3×30 mL)
- washThe combined extracts were washed with water, brine
- dry with materialdried over MgSO4 (anhydrous)
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by Biotage
Sources & evidence
- ORD record
- ord-a022289c9ece419ba783df9f21dce974
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193363B2
Reaction notes
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