Hydrochloric Acid → HCID 9979667, compound

HRID 421024Notes

Reaction equation

HRID 421024 reaction equation
[CH:1]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([N:11]=[C:12]=[O:13])=[CH:3][C:2]=1[C:14]([F:17])([F:16])[F:15].[Cl:18][C:19]1[CH:27]=[C:26]2[C:22]([CH2:23][C:24](=[O:28])[NH:25]2)=[CH:21][CH:20]=1.Cl>O1CCCC1.C(N(CC)CC)C>[F:17][C:14]([F:15])([F:16])[C:2]1[CH:3]=[C:4]([NH:11][C:12]([C:23]2[C:22]3[C:26](=[CH:27][C:19]([Cl:18])=[CH:20][CH:21]=3)[NH:25][C:24]=2[OH:28])=[O:13])[CH:5]=[C:6]([C:7]([F:10])([F:8])[F:9])[CH:1]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 27333143,5-Bis(trifluoromethyl)phenyl isocyanate

Product 1

HCID 9979667HCID 9979667, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

Under argon atmosphere, 3,5-bis(trifluoromethyl)isocyanate (255 mg, 1.0 mmol) was dissolved in tetrahydrofuran (5 mL). A solution of 6-chloro-oxindole (184 mg, 1.1 mmol) in tetrahydrofuran (5 ml) and triethylamine (0.3 mL) were added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (172.2 mg, 40.7%) as a pink solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-4439cdd7b9dd4d138986a56fb2e2e9af
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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