Water → HCID 178464144, compound

HRID 1170448Notes

Reaction equation

HRID 1170448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([O:34][Si](CC)(CC)CC)[C:17]2[C:12](=[CH:13][C:14](I)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33].[CH3:42][S-:43].[Na+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.O>C1(C)C=CC=CC=1.[Cu](I)I>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([OH:34])[C:17]2[C:12](=[CH:13][C:14]([S:43][CH3:42])=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33]

Participants

7

Reactant 4

HCID 962WaterHCID 13181,10-PhenanthrolineHCID 4378561Sodium methanethiolateHCID 178464150HCID 178464150, compound

Product 1

HCID 178464144HCID 178464144, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(2-chloro-6-fluorophenyl)-1-[trans-3-(diethylamino)-cyclobutylmethyl]-4-trifluoromethyl-3-triethylsilyloxy-6-iodo-1,3-dihydro-2H-indol-2-one (200 mg, 0.276 mmol) in toluene (1.0 mL) were added sodium thiomethoxide (193 mg, 2.76 mmol), 1,10-phenanthroline (5 mg, 0.028 mmol) and copper iodide (5 mg, 0.028 mmol), and the mixture was stirred at 100° C. for 3 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then filtered, concentrated and purified by silica gel column chromatography (chloroform/methanol=10/1). To a solution of the resulting oil in tetrahydrofuran (1 mL) was added tetrabutylammonium fluoride (excess amount). The mixture was stirred at room temperature for 3 hours, and then the reaction solution was concentrated and purified by silica gel column chromatography (chloroform/methanol=10/1) to give the titled compound (122 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (chloroform/methanol=10/1)
  6. additionTo a solution of the resulting oil in tetrahydrofuran (1 mL) was added tetrabutylammonium fluoride (excess amount)
  7. stirringThe mixture was stirred at room temperature for 3 hours
  8. concentrationthe reaction solution was concentrated
  9. custompurified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-b28ac5dd89c94550a26ac3dc1d224337
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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