Trifluoroacetic acid → HCID 66720879, compound

HRID 1639934Notes

Reaction equation

HRID 1639934 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][C:10]=1[C:18]1[CH:19]=[CH:20][C:21]([C:41]([O:43][CH3:44])=[O:42])=[N:22][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([O:31]CC2C=CC(OC)=CC=2)[CH:25]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][C:10]=1[C:18]1[CH:19]=[CH:20][C:21]([C:41]([O:43][CH3:44])=[O:42])=[N:22][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([OH:31])[CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66720882HCID 66720882, compound

Product 1

HCID 66720879HCID 66720879, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add 1 mL (13 mmol) of trifluoroacetic acid to a solution of 700 mg (1.3 mmol) of methyl 5-(2-chloro-5-ethoxyphenyl)-6-{4-chloro-3-[(4-methoxybenzyl)oxy]phenyl}pyridine-2-carboxylate in 10 mL of DCM stirred at 0° C. Stir the reaction mixture for 2 h at 20° C. then concentrate under reduced pressure. Take up the residue in 50 mL of DCM and wash with 50 mL of a saturated aqueous solution of NaHCO3. Dry the organic phase over Na2SO4 and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/EtOAc gradient from 0 to 30% of EtOAc. After concentration under reduced pressure, we obtain 524 mg of methyl 5-(2-chloro-5-ethoxyphenyl)-6-(4-chloro-3-hydroxyphenyl)pyridine-2-carboxylate in the form of oil.

Workup

  1. stirringStir the reaction mixture for 2 h at 20° C.
  2. concentrationthen concentrate under reduced pressure
  3. washwash with 50 mL of a saturated aqueous solution of NaHCO3
  4. dry with materialDry the organic phase over Na2SO4
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue
  7. customobtained by silica gel column chromatography
  8. washeluting with a cyclohexane/EtOAc gradient from 0 to 30% of EtOAc
  9. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-3c2da43b6d2143a2a09d5573f6386806
Source dataset
uspto-grants-2012_02
Patent number
US08110579B2

Reaction notes

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