Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=O)[CH2:11]Br)[S:7][CH:6]=1)=[O:4].S(=O)(=O)(O)O.[CH:19]([NH2:21])=[O:20]>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[N:21]=[CH:19][O:20][CH:11]=2)[S:7][CH:6]=1)=[O:4]Participants
4
Conditions
- Temperature
- 150 °C
Procedure
5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester (0.60 g, 2.28 mmol) was suspended in formamide (10 mL) then sulfuric acid (1 mL) was added and the tube purged with nitrogen then sealed. The mixture was heated at 150° C. by microwave irradiation for 15 minutes. The resultant solution was diluted with HCl (1 N) and water and extracted with ethyl acetate (×3). The organic phase was dried over sodium sulfate and evaporated then purified by chromatography on a silica II cartridge, eluting with 1:1 DCM:cyclohexane to afford 5-oxazol-4-yl-thiophene-3-carboxylic acid methyl ester as a pale yellow solid (0.197 g). LCMS m/z 210.14 [M+H]+ R. T.=3.64 min (Analytical Method 9).
Workup
- customthe tube purged with nitrogen
- customthen sealed
- additionThe resultant solution was diluted with HCl (1 N) and water
- extractionextracted with ethyl acetate (×3)
- dry with materialThe organic phase was dried over sodium sulfate
- customevaporated
- customthen purified by chromatography on a silica II cartridge
- washeluting with 1:1 DCM
Sources & evidence
- ORD record
- ord-81f9109593554d81b4f5f8e543e1fb83
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08614209B2
Linked notes
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