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Sodium Carbonate → 1h-Indole,2-methyl-5-phenyl-1-(phenylsulfonyl)-

HRID 400613
Notes
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Reaction equation

HRID 400613 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH3:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[OH-].[NH4+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH3:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 152568981-benzenesulfonyl-5-bromo-2-methyl-1H-indole

Product 1

HCID 600264171h-Indole,2-methyl-5-phenyl-1-(phenylsulfonyl)-Yield 91.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 1140TolueneSolvent
HCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 1-benzenesulfonyl-5-bromo-2-methyl-1H-indole (810 mg, 2.31 mmol), phenylboronic acid (850 mg, 6.97 mmol) and tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.029 mmol) in 20 mL of toluene, 10 mL of ethanol, and 5 mL of 2 M sodium carbonate was warmed at reflux for 4 hours. The reaction was monitored by TLC (ethyl acetate-hexanes (5:95), 2× developed; and toluene-hexanes (1:1)) indicating a slightly more polar product. The mixture was cooled and diluted with 12% aqueous ammonium hydroxide solution and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with three 15 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was adsorbed onto silica gel and chromatographed on silica gel using ethyl acetate-hexanes (1:99, then 2:98, then 3:97) to afford 731 mg (91% yield) of 1-benzenesulfonyl-2-methyl-5-phenyl-1H-indole.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with three 15 mL portions of ethyl acetate
  5. washThe combined organic layers were washed with three 15 mL portions of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel

Sources & evidence

ORD record
ord-56869d8437494037a97fbf4ed767859a
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08741897B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes