Trifluoroacetic acid → HCID 67044191, compound

HRID 1944447Notes

Reaction equation

HRID 1944447 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[CH:21]=[C:20]1[CH3:29].[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[S:38]([C:41]1[C:46]([CH:47]=O)=[CH:45][CH:44]=[CH:43][N:42]=1)(=[O:40])=[O:39]>ClCCl.ClCCCl>[CH3:15][O:16][C:17](=[O:30])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[C:21]([CH2:47][C:46]2[C:41]([S:38]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[Cl:31])(=[O:40])=[O:39])=[N:42][CH:43]=[CH:44][CH:45]=2)=[C:20]1[CH3:29]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetateHCID 86652196HCID 86652196, compound

Product 1

HCID 67044191HCID 67044191, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of triethylsilane (0.76 mL), trifluoroacetic acid (0.61 mL) and 1,2-dichloroethane (3.0 mL) at −10° C. was treated dropwise with a mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (0.070 g), 2-(2-chlorobenzenesulfonyl)-pyridine-3-carbaldehyde (0.089 g) and 1,2-dichloroethane (6.0 mL), and the resulting mixture was stirred at −10° C. for 15 minutes and then at room temperature for 4 hours. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (1:4 to 4:1 by volume). Further purification by crystallisation from ethyl acetate and pentane gave the title compound as a white solid (0.11 g).

Workup

  1. waitat room temperature for 4 hours
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate and pentane (1:4 to 4:1 by volume)
  7. customFurther purification
  8. customby crystallisation from ethyl acetate and pentane

Sources & evidence

ORD record
ord-0149da9f719b48cb978d0f0432585d9a
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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