Pyridine → HCID 86611445, compound

HRID 1865100Notes

Reaction equation

HRID 1865100 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16]([O:18][C:19]([C:21]1[N:22]([CH3:36])[C:23]([CH3:35])=[C:24]([C:33]#[N:34])[C:25]=1[C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)=[O:20])[CH3:17].N1C=CC=CC=1>C(Cl)Cl>[CH2:16]([O:18][C:19]([C:21]1[N:22]([CH3:36])[C:23]([CH3:35])=[C:24]([C:33]#[N:34])[C:25]=1[C:26]1[CH:31]=[CH:30][C:29]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:28][CH:27]=1)=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 69019512HCID 69019512, compound

Product 1

HCID 86611445HCID 86611445, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add trifluoromethanesulfonic anhydride (1.2 Eq.) to 4-cyano-3-(4-hydroxy-phenyl)-1,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (prepared in example E-238) and pyridine (1.5 Eq) in methylene chloride dropwise with stirring at 0° C. Stir the reaction mixture for 2 hours and then allow the reaction to warm to room temperature. Wash the organic layer with 1.0 N HCl, water, dry over potassium carbonate, filter, and concentrate under reduced vacuum. Purify the residue by silica gel chromatography (Chromatotron™) eluting with methylene chloride to provide the title compound as a yellow solid. Mass spectrum (m/e): 417.1 (M*+1): (Bruker 300) 1H NMR (CDCl3) δ 7.29-7.32 (2H, d), 7.27-7.29 (2H, d), 4.01-4.11 (2H, dd), 3.85-3.89 (3H, s), 2.43-2.47 (3H, s), 0.90-1.00 (3H, t).

Workup

  1. stirringStir the reaction mixture for 2 hours
  2. customthe reaction
  3. temperatureto warm to room temperature
  4. washWash the organic layer with 1.0 N HCl, water
  5. dry with materialdry over potassium carbonate
  6. filtrationfilter
  7. concentrationconcentrate under reduced vacuum
  8. customPurify the residue by silica gel chromatography (Chromatotron™)
  9. washeluting with methylene chloride

Sources & evidence

ORD record
ord-3e29aebccf424ac89ccdc95c222b62ee
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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