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

HRID 1418075Notes

Reaction equation

HRID 1418075 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-29f45cba254743b6b8092bf1e579f50f
Source dataset
uspto-grants-1999_03
Patent number
US05880140

Reaction notes

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