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

HRID 1418425Notes

Reaction equation

HRID 1418425 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][N:7]=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([N:57]1[CH:61]=[C:60]([CH2:62][C:63]2[CH:68]=[CH:67][C:66]([C:69]#[N:70])=[CH:65][CH:64]=2)[N:59]=[CH:58]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:59]2[C:60]([CH2:62][C:63]3[CH:68]=[CH:67][C:66]([C:69]#[N:70])=[CH:65][CH:64]=3)=[CH:61][N:57]=[CH:58]2)=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 15411145(6-Thien-2-ylpyrid-3-yl)methanolHCID 158375331-Trityl-4-(4-cyanobenzyl)imidazole

Product 1

HCID 99067091-(2-(Thien-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-(thien-2-yl)-5-hydroxymethylpyridine (255 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-bf3697adbfb64a4dbdec293f7204f8f8
Source dataset
uspto-grants-1999_03
Patent number
US05883105

Reaction notes

Loading…