Dimethylformamide → HCID 58148287, compound
Reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[OH:19])=[N:10][C:9]=2[CH:20]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH:32](I)([CH3:34])[CH3:33]>O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[O:19][CH:32]([CH3:34])[CH3:33])=[N:10][C:9]=2[CH:20]=1)([CH3:4])([CH3:2])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 0.30 g of 4-(5-tert-butylbenzoxazole-2-yl)pyridin-3-ol, 0.17 g of potassium carbonate and 3 ml of DMF, 0.21 g of isopropyl iodide was added at room temperature. The reaction mixture was stirred while heating at 60° C. for two hours. The mixture was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.21 g of 5-tert-butyl-2-(3-isopropoxypyridin-4-yl)benzoxazole (hereinafter, referred to as “active compound 104”).
Workup
- additionwas added at room temperature
- temperatureThe mixture was cooled to room temperature
- extractionfollowed by extraction with ethyl acetate twice
- washThe combined organic layers were washed with a saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-76da32d9cca645ccb3aa2df32e10a9e0
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609705B2
Reaction notes
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