Trifluoroacetic acid → Ethyl 9-bromo-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate
Reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:29]=[CH:28][C:12]2[O:13][CH2:14][C:15](O)([CH3:26])[C:16]3[S:20][C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:18][C:17]=3[C:11]=2[CH:10]=1.[SiH](CC)(CC)CC>ClCCl>[Br:8][C:9]1[CH:29]=[CH:28][C:12]2[O:13][CH2:14][CH:15]([CH3:26])[C:16]3[S:20][C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:18][C:17]=3[C:11]=2[CH:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
TFA (891 mg, 7.88 mmol, 30.00 equiv) was added dropwise to a stirred solution of ethyl 9-bromo-4-hydroxy-4-methyl-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (100 mg, 0.26 mmol, 1.00 equiv) and Et3SiH (454 mg, 3.90 mmol, 15.00 equiv) in dichloromethane (5 mL) at 0° C. After being stirred at room temperature overnight the reaction was quenched with 10 mL of saturated NaHCO3, extracted with 5×20 mL of ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:15) to give 70 mg (73%) of the titled compound as a light yellow solid; LC-MS (ES, m/z) 368, 369 [M+11]+.
Workup
- customwas quenched with 10 mL of saturated NaHCO3
- extractionextracted with 5×20 mL of ethyl acetate
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:15)
Sources & evidence
- ORD record
- ord-bf7f068819d24b2f966bd7a9e3c8c43a
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
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