Hydrochloric Acid → HCID 66841960, compound

HRID 1158834Notes

Reaction equation

HRID 1158834 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3Br)=[CH:14][N:15]2[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:36]([O:38]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:37].Cl>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:35])[N:7]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:36](=[O:38])[CH3:37])=[CH:14][N:15]2[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 66842178HCID 66842178, compound

Product 1

HCID 66841960HCID 66841960, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

i)—A solution of [3-(2-bromo-phenylsulfanyl)-1-(3,5-difluoro-benzyl)-1H-indol-6-yl]-methyl-carbamic acid tert-butyl ester (Example 6, method 2, step i; 1.00 g, 1.79 mmol) in toluene (oxygen-free, 25 ml), containing dichlorobis(triphenylphosphine)palladium(II) (0.076 g, 0.0672 mmol) and (1-ethoxyvinyl)tributyltin (0.824 ml, 2.44 mmol) was heated under reflux overnight. After cooling, hydrochloric acid (2M, 15 ml) was added and the mixture was stirred for 1 h. The mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (heptane/ethyl acetate 9:1→85:15) afforded [3-(2-acetyl-phenylsulfanyl)-1-(3,5-difluoro-benzyl)-1H-indol-6-yl]-methyl-carbamic acid tert-butyl ester (0.245 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customThe mixture was quenched with a saturated aqueous solution of sodium hydrogencarbonate
  5. extractionthe product was extracted into ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da3101f43da54cca82b67ba61f4b55b2
Source dataset
uspto-grants-2010_10
Patent number
US07812036B2

Reaction notes

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