Trifluoroacetic acid → HCID 68917014, compound

HRID 2111630Notes

Reaction equation

HRID 2111630 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:5]2([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:5]2=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 23084562HCID 23084562, compound

Product 1

HCID 68917014HCID 68917014, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

The product of above-mentioned (10-a) (0.23 g, 0.69 mmol) was added into a mixed solvent of methylene chloride (3.5 ml) and trifluoroacetic acid (1.4 ml), and triethylsilane (0.15 ml, 0.96 mmol) was added dropwise thereto, followed by stirring at 25° C. for 2 hrs. The reaction solution was added into 1N aqueous K2CO3 solution, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:acetone=5:1) to give 91 mg of 5,6-dimethyl-3-hexylidene-2-(3-pyridyl)isoindolin-1-one.

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (chloroform:acetone=5:1)

Sources & evidence

ORD record
ord-0d308e4265814e5ea8a7e6ae23d71813
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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