Hydrochloric Acid → HCID 9979667, compound

HRID 2384327Notes

Reaction equation

HRID 2384327 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-d819804748004a788fecb8bfed95b786
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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