Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile

HRID 641878Notes

Reaction equation

HRID 641878 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=3)[NH:12][CH:11]=2)[CH2:6][CH2:5]1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH3:3][N:4]1[CH2:5][CH:6]=[C:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=3)[N:12]([S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])[CH:11]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 149732163-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile

Product 1

HCID 534146671-(Benzenesulfonyl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrileYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (26 mg, 1.07 mmol) was added in several batches to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile (200 mg, 0.76 mmol) in DMF (2 mL) at 0-5° C., and the mixture was maintained for 1 hour at room temperature. Benzenesulfonyl chloride (222 mg, 1.24 mmol) was then added, and the resulting solution was maintained at room temperature for an additional 4 hours. The mixture was filtered, and the filter cake was washed with ethanol (2×10 mL) and diethylether (2×10 mL) to afford 250 mg (86%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indole-5-carbonitrile as a white solid. 1H NMR (DMSO) δ 8.41 (s, 1H), 8.14 (d, 2H), 8.07 (d, 2H), 7.78 (d, 1H), 7.71 (d, 2H), 7.61 (t, 1H), 6.35 (s, 1H), 3.79 (2H), 3.34 (s, 2H), 2.80-2.87 (m, 5H).

Workup

  1. temperaturethe resulting solution was maintained at room temperature for an additional 4 hours
  2. filtrationThe mixture was filtered
  3. washthe filter cake was washed with ethanol (2×10 mL) and diethylether (2×10 mL)

Sources & evidence

ORD record
ord-9aa442031b4d41aa87163d5ce936a083
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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