Trifluoromethanesulfonic anhydride → {4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-ynyl}-(2-methoxy-ethyl)-methyl-amine

HRID 966265노트

반응식

HRID 966265 반응식
[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]=1

참가 물질

6

반응물 4

HCID 67749Trifluoromethanesulfonic anhydride2회HCID 81531Diisopropylethylamine2회HCID 300977(2-Methoxyethyl)(methyl)amineHCID 223139024-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-yn-1-ol

생성물 1

HCID 22313996{4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-ynyl}-(2-methoxy-ethyl)-methyl-amine수율 56%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  1. stirringstirring
  2. waitcontinued for 1 h
  3. stirringstirred for 1.5 h
  4. washwashed with Na2CO3 solution, brine
  5. dry with materialdried with Na2SO4

출처 및 근거

ORD 기록
ord-c167bc30470d475ab1b0fba73035c477
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951879B2

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