Dichloromethane → HCID 10401571, compound

HRID 1159795Notes

Reaction equation

HRID 1159795 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12].[CH:20]([SnH3])=[CH2:21].C(Cl)Cl>C1(C)C=CC=CC=1>[C:14]1([S:11]([N:6]2[C:7]3[C:3](=[C:2]([CH:20]=[CH2:21])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:5]2)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 220153114-Bromo-1-(phenylsulfonyl)-1H-indole2×HCID 71365144HCID 71365144, compound

Product 1

HCID 10401571HCID 10401571, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4-Bromo-1-(phenylsulfonyl)-1H-indole (8.52 g, 25.3 mmol, Intermediate 44) was dissolved in dry toluene (20 mL) under an N2(g) atmosphere before vinylstannane (16.07 g, 50.7 mmol) and bis[triphenylphosphine)palladium(II) acetate (0.95 g, 1.3 mmol) was added. The reaction was heated to 110° C. for 16 h cooled the reaction mixture to RT and filtered the reaction mixture through a celite pad, and evaporated the solvent. Dissolved the obtained oil in acetonitrile and hexanes, separated the phases. Evaporated the acetonitrile phase and purified the obtained crude product by flash chromatography using 30% DCM in hexanes. Isolated 4.4 g of the desired product as a white solid, yield 62%. MS (ESI+) for C16H13NO2S m/z 284 (M+H)+.

Workup

  1. additionwas added
  2. temperaturecooled the reaction mixture to RT
  3. filtrationfiltered the reaction mixture through a celite pad
  4. customevaporated the solvent
  5. dissolutionDissolved the obtained oil in acetonitrile
  6. customhexanes, separated the phases
  7. customEvaporated the acetonitrile phase
  8. custompurified the
  9. customobtained crude product by flash chromatography

Sources & evidence

ORD record
ord-df2c5e4869b1414d83af98fbc6024fa3
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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