Water → HCID 58158492, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:26]1[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[N:30][CH:31]=1.O>CN(C)C=O>[N+:32]([C:29]1[N:30]=[CH:31][C:26]([O:1][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:4][CH:3]=2)=[CH:27][CH:28]=1)([O-:34])=[O:33]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of benzyl (4-hydroxyphenyl)carbamate (1.44 g, 5.91 mmol) in N,N-dimethylformamide (10 mL) were added cesium carbonate (2.41 g, 7.39 mmol) and 5-bromo-2-nitropyridine (1.0 g, 4.93 mmol), and the mixture was stirred at room temperature for 16 hr. Water (40 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran (=2/1, 120 mL). The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (NH silica gel, hexane/ethyl acetate=3/1→1/3) to give the title compound (1.01 g, 56%).
Workup
- extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran (=2/1, 120 mL)
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel chromatography (NH silica gel, hexane/ethyl acetate=3/1→1/3)
Sources & evidence
- ORD record
- ord-8bdbc792d39d4fb38e0d35b21070fd00
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445509B2
Reaction notes
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