Water → HCID 59586684, compound
Reaction equation
[CH2:1]([C:4]1[C:5](=[O:10])[NH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][CH3:3].CC(C)([O-])C.[K+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[O:27][CH3:28].O>CN(C=O)C>[CH3:28][O:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]1=[O:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
500 mg (3.65 mmol) of the product from example 51A are dissolved in 7.3 ml of DMF and cooled to 0° C. To this are added 613 mg (5.47 mmol) of potassium tert-butoxide, and the mixture is left to stir at RT for 30 min. Then 624 mg (3.65 mmol) of 1-fluoro-2-methoxy-4-nitrobenzene are added. The mixture is stirred at RT for 6 h, water is added and the mixture is extracted four times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated. Purification is effected by preparative HPLC. The resulting product fraction is purified further by chromatography on silica gel (eluent: dichloromethane, then 10:1 dichloromethane/methanol). This affords 158 mg (15% of theory) of the desired compound as a solid.
Workup
- waitthe mixture is left
- stirringThe mixture is stirred at RT for 6 h
- extractionthe mixture is extracted four times with ethyl acetate
- dry with materialThe combined organic phases are dried over sodium sulfate
- concentrationconcentrated
- customPurification
- customThe resulting product fraction is purified further by chromatography on silica gel (eluent
Sources & evidence
- ORD record
- ord-6e75dd30fafb405cb9ef102a1c8044be
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198267B2
Reaction notes
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