Tetrahydrofuran → 7-(2-hydroxyethylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one
Reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.[Si]([O:31][CH2:32][CH2:33][NH:34][C:35]1[CH:44]=[C:43]2[C:38]([CH:39]=[C:40]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]([F:55])([F:54])[F:53])[NH:41][C:42]2=[O:45])=[CH:37][CH:36]=1)(C(C)(C)C)(C)C.[Cl-].[NH4+]>C(OCC)(=O)C>[OH:31][CH2:32][CH2:33][NH:34][C:35]1[CH:44]=[C:43]2[C:38]([CH:39]=[C:40]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]([F:55])([F:53])[F:54])[NH:41][C:42]2=[O:45])=[CH:37][CH:36]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
TBAF (1 M THF solution, 88.2 μL, 0.882 mmol) was added to a THF solution (4 mL) that contained the 7-[2-(tert-butyldimethylsilanyloxy)ethylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (204 mg, 0.441 mmol) obtained in step A, and the obtained mixture was then stirred at a room temperature for 1 hour. Thereafter, the reaction solution was poured into a mixed solution of ethyl acetate and a saturated ammonium chloride aqueous solution. An organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1 to 10:1), so as to obtain 7-(2-hydroxyethylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (173 mg, quant).
Workup
- dry with materialAn organic layer was dried over anhydrous sodium sulfate
- distillationthe solvent was then distilled away under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1 to 10:1)
Sources & evidence
- ORD record
- ord-6b705908f65145929fe4c45b7bb3090a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820693B2
Reaction notes
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