Dimethylformamide → tert-Butyl (5-vinylthiazol-2-yl)carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[S:9][C:10](Br)=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].CN(C=O)C.[CH2:22]1COC[CH2:23]1>>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[S:9][C:10]([CH:22]=[CH2:23])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
(5-Bromo-thiazol-2-yl)-carbamic acid tert-butyl ester (0.200 g, 0.71 mmol), tetrakis(triphenylphospine)palladium (0.042 g, 0.036 mmol), lithium chloride (0.91 g, 2.14 mmol), and tributyl (vinyl)stannate (0.68 g, 2.14 mmol) were taken in 8 mL of THF and 8 mL of DMF and reflux for 2 hrs. After completion of reaction THF was removed under reduced pressure on ratavapour and the residue was partioned between ethyl acetate (20 mL) and water (20 mL). The layers were separated. Aq. Layer was extracted with ethyl acetate (2×20 mL). The combined organic layer was washed with brine and dried over anhydrous sodium sulfate filtered and concentrated under reduced pressure to get the crude product which was purified by preparative TLC to get the pure product (5-Vinyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.137 g).
Workup
- customwas removed under reduced pressure on ratavapour
- customThe layers were separated
- extractionAq. Layer was extracted with ethyl acetate (2×20 mL)
- washThe combined organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto get the crude product which
- customwas purified by preparative TLC
Sources & evidence
- ORD record
- ord-23a0bd2e14de4a5c9b7f308354152055
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340506B2
Reaction notes
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