Cesium carbonate → N-(1-adamantylmethyl)-5-bromo-2-[(2S)-oxiran-2-ylmethoxy]isonicotinamide
Reaction equation
S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:5][C@H:6]1[O:8][CH2:7]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[C:24]12([CH2:34][NH:35][C:36](=[O:45])[C:37]3[C:42]([Br:43])=[CH:41][N:40]=[C:39]([OH:44])[CH:38]=3)[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>CN(C)C=O.O>[C:24]12([CH2:34][NH:35][C:36](=[O:45])[C:37]3[C:42]([Br:43])=[CH:41][N:40]=[C:39]([O:44][CH2:5][C@@H:6]4[CH2:7][O:8]4)[CH:38]=3)[CH2:31][CH:30]3[CH2:32][CH:26]([CH2:27][CH:28]([CH2:29]3)[CH2:33]1)[CH2:25]2Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A suspension of (S)-glycidyl nosylate (0.29 g), caesium carbonate (1.82 g) and N-(1-adamantylmethyl)-5-bromo-2hydroxyisonicotinamide (0.41 g) (Example 35(ii)) in anhydrous N,N-dimethylformamide (6 ml) was heated at 60° C. under nitrogen for 2 hours. The reaction mixture was allowed to cool to room temperature, diluted with water (50 ml) and extracted into ethyl acetate (3×20 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with dichloromethane:ethyl acetate (4:1 to 0:1) to afford the sub-titled compound (0.12 g).
Workup
- temperatureto cool to room temperature
- extractionextracted into ethyl acetate (3×20 ml)
- dry with materialThe combined extracts were dried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel eluting with dichloromethane:ethyl acetate (4:1 to 0:1)
Sources & evidence
- ORD record
- ord-e15181aaf2c14b5b83c155b6b69396b0
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129246B2
Reaction notes
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