Ethyl Acetate → 2-Fluoro-4-(thiazol-2-yloxy)-phenylamine
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].Br[C:11]1[S:12][CH:13]=[CH:14][N:15]=1.CC([O-])(C)C.[K+].CCOC(C)=O>CC(N(C)C)=O>[F:9][C:3]1[CH:4]=[C:5]([O:8][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]Participants
6
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 427A (0.814 g, 6.41 mmol), 2-bromothiazole (1.0 g, 6.10 mmol) and t-BuOK (0.821 g, 7.32 mmol) in DMA (25 ml) was stirred at 150° C. under argon for 1 h, then cooled to rt. Treated with EtOAc (150 ml), the mixture was washed with H2O (50 ml), 3N NaOH (2×50 ml), H2O (50 ml), dried with Na2SO4. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (10%-25% EtOAc-hexanes) gave 427B (1.02 g, 80%) as a colorless oil. It has a retention time of 4.02 min (standard LC1 method, 8 min run). MS Found: (M+H)+=211.1
Workup
- temperaturecooled to rt
- washthe mixture was washed with H2O (50 ml), 3N NaOH (2×50 ml), H2O (50 ml)
- dry with materialdried with Na2SO4
- customRemoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-560dc87a25c94547af392d462a0bb19d
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030112B2
Reaction notes
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