1,1-Dichloroethane → HCID 67044582, compound

HRID 1944477Notes

Reaction equation

HRID 1944477 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.ClC(Cl)C.[C:19]1([N:25](COCC[Si](C)(C)C)[S:26]([C:29]2[C:34]([CH:35]=O)=[CH:33][CH:32]=[CH:31][N:30]=2)(=[O:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:45][O:46][C:47](=[O:60])[CH2:48][N:49]1[C:57]2[C:52](=[CH:53][C:54]([F:58])=[CH:55][CH:56]=2)[CH:51]=[C:50]1[CH3:59]>>[CH3:45][O:46][C:47](=[O:60])[CH2:48][N:49]1[C:57]2[C:52](=[CH:53][C:54]([F:58])=[CH:55][CH:56]=2)[C:51]([CH2:35][C:34]2[C:29]([S:26](=[O:27])(=[O:28])[NH:25][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:30][CH:31]=[CH:32][CH:33]=2)=[C:50]1[CH3:59]

Participants

6

Reactant 5

HCID 63651,1-Dichloroethane2×HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 86652206HCID 86652206, compound

Product 1

HCID 67044582HCID 67044582, compoundYield 32.6%

Procedure

A mixture of triethylsilane (3.1 mL), trifluoroacetic acid (0.88 mL) and dichloroethane (12 mL) at −15° C. was treated dropwise with a mixture of 3-formylpyridine-2-sulfonic acid phenyl[2-(trimethylsilanyl)ethoxymethyl]amide (0.55 g), (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.29 g) and dichloroethane (18 mL), and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane. The mixture was washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane, cyclohexane, ethyl acetate and methanol (9:1:0:0 to 0:0:9:1 by volume) to afford the title compound (0.20 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried 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 dichloromethane, cyclohexane, ethyl acetate and methanol (9:1:0:0 to 0:0:9:1 by volume)

Sources & evidence

ORD record
ord-0b4f29d1b2f2479dabe21bc0183fd74e
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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