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Sodium Carbonate → 3-(2-tert-butylphenyl)-1-(phenylsulfonyl)-1H-indole

HRID 2423217
Notes
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Reaction equation

HRID 2423217 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](B(O)O)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([CH3:37])([CH3:36])[CH3:35])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O.C(OCC)(=O)C.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:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:11]=1)([CH3:37])([CH3:36])[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27762171-(phenylsulfonyl)-1H-indol-3-ylboronic acidHCID 187792072-(Tert-butyl)phenyl trifluoromethanesulfonate

Product 1

HCID 672419373-(2-tert-butylphenyl)-1-(phenylsulfonyl)-1H-indoleYield 92%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

1-(Phenylsulfonyl)-1H-indol-3-ylboronic acid (150.9 mg, 0.501 mmol), 2-tert-butylphenyl trifluoromethanesulfonate (255 mg, 0.902 mmol) and tetrakis(triphenylphosphine)palladium (0) (58 mg, 0.050 mmol) are combined in a septa capped microwave vial and placed under an argon atmosphere. Degassed solutions of 2 M sodium carbonate (0.75 mL, 1.50 mmol) and of dioxane (2.5 mL) were introduced and the vial heated to 150° C. for 15 minutes in a microwave reactor. The cooled reaction mixture was diluted with water and ethyl acetate, the phases separated and the aqueous extracted twice more with ethyl acetate. The combined extracts were washed with water, brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with a gradient of ethyl acetate and hexanes to give 3-(2-tert-butylphenyl)-1-(phenylsulfonyl)-1H-indole (175.8 mg, 92%) as a colorless gummy solid.

Workup

  1. customcapped microwave vial
  2. customThe cooled reaction mixture
  3. customthe phases separated
  4. extractionthe aqueous extracted twice more with ethyl acetate
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-2feede511ec445e48403e3681e1b83cf
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960569B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes