Benzenesulfonyl chloride → Indole

HRID 641866Notes

Reaction equation

HRID 641866 reaction equation
[H-].[Na+].Br[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2C1CCN(C)CC=1.C1(S(Cl)(=O)=O)C=CC=CC=1>CN(C=O)C>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Product 1

HCID 798Indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

NaH (600 mg, 15.00 mmol) was added (in several batches) to a solution of 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (3 g, 9.79 mmol) in DMF (60 mL) while cooling to a temperature of 0-5° C. The resulting solution was stirred for 1 hour while the temperature was maintained at room temperature. Benzenesulfonyl chloride (2.3 g, 12.89 mmol) was then added dropwise and the reaction was stirred for an additional 4 hours at room temperature. After filtration, the filter cake was washed with ethanol (2×50 mL) and the resulting solid was dried to afford 0.4 g (10%) of 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-phenylsulfonyl)-1H-indole as a white solid. 1H NMR (DMSO) δ 8.04 (4H), 7.95 (1H), 7.73 (1H), 7.32-7.63 (3H), 6.29 (s, 1H), 3.98 (2H), 3.68 (2H), 2.72-2.89 (5H). m/z 434.1 (M++1)

Workup

  1. temperaturewas maintained at room temperature
  2. stirringthe reaction was stirred for an additional 4 hours at room temperature
  3. filtrationAfter filtration
  4. washthe filter cake was washed with ethanol (2×50 mL)
  5. customthe resulting solid was dried

Sources & evidence

ORD record
ord-bc028d9586ae47aeb4113da8088c3392
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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