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

HRID 270359ノート

反応式

HRID 270359 の反応式
[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

参加物

6

反応物 4

HCID 67749Trifluoromethanesulfonic anhydride2 回HCID 81531Diisopropylethylamine2 回HCID 300977(2-Methoxyethyl)(methyl)amineHCID 223139024-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-yn-1-ol

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fb33e9b4fe3245e1a79aa7d6f5034eda
出典データセット
uspto-grants-2008_11
特許番号
US07449483B2

反応ノート

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