Trifluoromethanesulfonic anhydride → 1-(2-(Pyrid-2-yl) pyrid-5-ylmethyl)-5-(4-cyanobenzyl)imidazole

HRID 1418075ノート

反応式

HRID 1418075 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][N:8]=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([N:58]1[CH:62]=[C:61]([CH2:63][C:64]2[CH:69]=[CH:68][C:67]([C:70]#[N:71])=[CH:66][CH:65]=2)[N:60]=[CH:59]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:60]2[C:61]([CH2:63][C:64]3[CH:69]=[CH:68][C:67]([C:70]#[N:71])=[CH:66][CH:65]=3)=[CH:62][N:58]=[CH:59]2)=[CH:9][N:8]=1

参加物

6

反応物 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 10352407[6-(Pyridin-2-yl)pyridin-3-yl]methanolHCID 158375331-Trityl-4-(4-cyanobenzyl)imidazole

生成物 1

HCID 98848271-(2-(Pyrid-2-yl) pyrid-5-ylmethyl)-5-(4-cyanobenzyl)imidazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 2-(pyrid-2-yl)-5-hydroxymethyl-pyridine (269 mg, 1.33 mmol) and diisopropylethylamine (0.464 mL, 2.66 mmol) in dichloromethane (7 mL) at -78° C. is added trifluoromethanesulfonic anhydride (0.224 mL, 1.33 mmol) and the mixture stirred at -78° C. for 1 hour. To this mixture is added a solution of 1-trityl-4-(4-cyanobenzyl)-imidazole (566 mg, 1.33 mmol) in dichloromethane (5 mL). The mixture is allowed to warm to ambient temperature and stirred for 2 hours. The solvent is evaporated in vacuo. The residue is dissolved in methanol (50 mL), heated at reflux for 1 hour, and the solvent is evaporated in vacuo. The residue is partitioned between dichloromethane and sat. aq. NaHCO3 solution. The organic layer is dried, (Na2SO4) and the solvent evaporated in vacuo. The residue is chromatographed to afford the title compound.

後処理

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 2 hours
  3. customThe solvent is evaporated in vacuo
  4. dissolutionThe residue is dissolved in methanol (50 mL)
  5. temperatureheated
  6. temperatureat reflux for 1 hour
  7. customthe solvent is evaporated in vacuo
  8. customThe residue is partitioned between dichloromethane and sat. aq. NaHCO3 solution
  9. customThe organic layer is dried
  10. custom(Na2SO4) and the solvent evaporated in vacuo
  11. customThe residue is chromatographed

出典と根拠

ORDレコード
ord-29f45cba254743b6b8092bf1e579f50f
出典データセット
uspto-grants-1999_03
特許番号
US05880140

反応ノート

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