1,1-Dichloroethane → HCID 67044040, compound

HRID 1944409Notes

Reaction equation

HRID 1944409 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15].[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[S:22]([C:25]1[CH:29]=[CH:28][S:27][C:26]=1[CH:30]=O)(=[O:24])=[O:23].ClC(Cl)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(=O)([O-])O.[Na+]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:30][C:26]2[S:27][CH:28]=[CH:29][C:25]=2[S:22]([C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)(=[O:23])=[O:24])=[C:6]1[CH3:15]

Participants

7

Reactant 5

HCID 63651,1-Dichloroethane2×HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 86652187HCID 86652187, compound

Product 1

HCID 67044040HCID 67044040, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.14 g), 3-(thiophene-2-sulfonyl)thiophene-2-carbaldehyde (0.12 g) and dichloroethane (5.0 mL) at 0° C. was treated dropwise with a mixture of triethylsilane (1.4 mL), trifluoroacetic acid (0.35 mL) and dichloroethane (2.0 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was cooled to 0° C., diluted with saturated aqueous sodium hydrogen carbonate solution and the phases separated. The aqueous phase was extracted with dichloromethane and the combined organic solution was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 1:1 by volume), to afford the title compound as a yellow solid (0.17 g).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic solution was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 1:1 by volume)

Sources & evidence

ORD record
ord-82f92c0fd65e41bcae1555b5ef57f3a0
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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