Sodium Carbonate → 5-[2-(methylthio)phenyl]-1H-indole

HRID 2083987Notes

Reaction equation

HRID 2083987 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:21][S:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 881662-BromothioanisoleHCID 27343615-Indolylboronic acid

Product 1

HCID 121488205-[2-(methylthio)phenyl]-1H-indoleYield 52.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5-indoleboronic acid (2.0 g, 12 mmol) and 2-bromothioanisole (1.6 mL, 12 mmol) in a mixture of ethylene glycol dimethyl ether (20 mL) and aqueous sodium carbonate (10 mL) was deoxygenated by a rapid stream of nitrogen applied to the system for 20 min, then treated with Pd(0) at once. The reaction was refluxed for 18 h, cooled down, filtered through Celite® and washed with THF (20 mL). The filtrate evaporated to dryness, taken up in water and extracted with EtOAc (3×). The EtOAc extracts were dried over sodium sulfate and concentrated. The crude residue was purified by flash chromatography (hexane/EtOAc, 1:3) to afford 5-[2-(methylthio)phenyl]-1H-indole (1.5 g, 52%).

Workup

  1. customwas deoxygenated by a rapid stream of nitrogen
  2. additiontreated with Pd(0) at once
  3. temperatureThe reaction was refluxed for 18 h
  4. temperaturecooled down
  5. filtrationfiltered through Celite®
  6. washwashed with THF (20 mL)
  7. customThe filtrate evaporated to dryness
  8. extractionextracted with EtOAc (3×)
  9. dry with materialThe EtOAc extracts were dried over sodium sulfate
  10. concentrationconcentrated
  11. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 1:3)

Sources & evidence

ORD record
ord-49fbeb56ad414edc806ba8f846f744c1
Source dataset
uspto-grants-2004_04
Patent number
US06716841B2

Reaction notes

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