Sodium Azide → 4-(2-((3-(Azidomethyl)oxetan-3-yl)methoxy)-3,4-dimethoxyphenyl)-indan-1-one
Reaction equation
CS(O[CH2:6][C:7]1([CH2:11][O:12][C:13]2[C:18]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH2:21][CH2:22][C:23]4=[O:28])=[CH:17][CH:16]=[C:15]([O:29][CH3:30])[C:14]=2[O:31][CH3:32])[CH2:10][O:9][CH2:8]1)(=O)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C)C=O>[N:33]([CH2:6][C:7]1([CH2:11][O:12][C:13]2[C:14]([O:31][CH3:32])=[C:15]([O:29][CH3:30])[CH:16]=[CH:17][C:18]=2[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[CH2:10][O:9][CH2:8]1)=[N+:34]=[N-:35]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of (3-((2,3-dimethoxy-6-(1-oxo-2,3-dihydro-1H-inden-4-yl)phenoxy)methyl)oxetan-3-yl)methyl methanesulfonate (5 g, 10.82 mmol) in dimethylformamide (40 mL), was added sodium azide (3.5 g, 54.11 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 4-(2-((3-(azidomethyl)oxetan-3-yl)methoxy)-3,4-dimethoxyphenyl)-indan-1-one as a solid.
Workup
- customthe resultant reaction mixture
- customThe reaction mixture was quenched with ice water
- extractionextracted with ethyl acetate (3×)
- washThe combined ethyl acetate layer was washed with brine
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d18b2d3526954c5a96d5e87f5dc640d8
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051290B2
Reaction notes
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