Trifluoromethanesulfonic anhydride → {4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-ynyl}-(2-methoxy-ethyl)-methyl-amine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH2:19]CO)=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:22][CH2:23][N:24]([CH:28](C)C)[CH:25](C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:46][O:47]CCNC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH2:19][CH2:25][N:24]([CH2:23][CH2:22][O:47][CH3:46])[CH3:28])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
100 mg (0.28 mmol) ) 4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-yn-1-ol in 2 ml CH2Cl2 were treated with 53 μl (0.31 mmol) Huenig's base at 51 μl (0.31 mmol) trifluoromethane sulfonic acid anhydride at −15° C. The solution was stirred at that temperature for 1 h, additional 10 μl trifluoromethane sulfonic acid anhydride were added and stirring continued for 1 h. 48 μl (0.28 mmol) Huenig's base and 75 μl (0.84 mmol) N-(2-Methoxyethyl)methylamine were added at −15° C. The solution was warmed to RT and stirred for 1.5 h. The solution was diluted with CH2Cl2 and washed with Na2CO3 solution, brine and dried with Na2SO4. Column chromatography gave 66.1 mg (56%) {4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-ynyl}-(2-methoxy-ethyl)-methyl-amine as brown oil, MS: 429 (MH+, 1Br).
Workup
- stirringstirring
- waitcontinued for 1 h
- stirringstirred for 1.5 h
- washwashed with Na2CO3 solution, brine
- dry with materialdried with Na2SO4
Sources & evidence
- ORD record
- ord-c167bc30470d475ab1b0fba73035c477
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06951879B2
Reaction notes
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