Benzene → HCID 117770120, compound

HRID 1526342Notes

Reaction equation

HRID 1526342 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13]([CH:14]=O)=[CH:12][C:11]2[NH:16][N:17]=[C:18]([N:19]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])[C:10]=2[C:9]1=[O:30].FC(F)(F)C([NH:35]OC(C(F)(F)F)=O)=O.N1C=CC=CC=1.C1C=CC=CC=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13]([C:14]#[N:35])=[CH:12][C:11]2[NH:16][N:17]=[C:18]([N:19]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:29])[C:10]=2[C:9]1=[O:30]

Participants

6

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 69634(2,2,2-Trifluoroacetyl)azanyl 2,2,2-trifluoroacetateHCID 117770350HCID 117770350, compound

Product 1

HCID 117770120HCID 117770120, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(2-chlorophenyl)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-6-carbaldehyde obtained in Step J (260 mg), 2,2,2-trifluoro-N-(2,2,2-trifluoroacetoxyl)acetamide (140 mg), pyridine (0.100 mL) and benzene (3.10 mL) was refluxed for 1 hr, and cooled to room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (203 mg).

Workup

  1. temperaturewas refluxed for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c9ab7b65b8c44ca5aa2df40c3ac44bdf
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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