(4-Methoxyphenyl)boronic acid → 1-(Benzenesulfonyl)-3-(4-methoxyphenyl)-1H-indole

HRID 2370981Notes

Reaction equation

HRID 2370981 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>COCCOC.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>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:3]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 201262(4-Methoxyphenyl)boronic acidHCID 516892Sodium BicarbonateHCID 27762153-Bromo-(1-phenylsulfonyl)indole

Product 1

HCID 671088721-(Benzenesulfonyl)-3-(4-methoxyphenyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

3-bromo-1-(phenylsulfonyl)-1H-indole (500 mg, 1.49 mmol) and 5 mol % tetrakis(triphenylphosphine)palladium were mixed in 9 ml degassed DME. The mixture was stirred for 5 min under nitrogen and was then heated to 85° C. 4-Methoxyphenyl boronic acid (1.2 eq) dissolved in 3 ml DME and 5.95 ml sodium hydrogen carbonate (1 M) were simultaneously added drop wise at 85° C. over 5 min. The reaction was stirred at 85° C. for 10 min and then cooled to room temperature. DME was concentrated, water was added and the remaining aqueous mixture was extracted with DCM. The combined organic layers were concentrated and the crude product was purified on silica using EtOAc/n-heptane (1:9 to 2:8) as eluents. 363 mg 3-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-indole was obtained as white crystals.

Workup

  1. customdegassed DME
  2. customwise at 85° C.
  3. customover 5 min
  4. stirringThe reaction was stirred at 85° C. for 10 min
  5. temperaturecooled to room temperature
  6. concentrationDME was concentrated
  7. additionwater was added
  8. extractionthe remaining aqueous mixture was extracted with DCM
  9. concentrationThe combined organic layers were concentrated
  10. customthe crude product was purified on silica

Sources & evidence

ORD record
ord-0b3f891fb9654d368c6e346b6655dedc
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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