4-Toluenesulfonyl chloride → (R)-5-bromo-3-(1-methyl-2-pyrrolidinylmethyl)-1-tosyl-1H-indole

HRID 651712Notes

Reaction equation

HRID 651712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].[OH-].[K+].[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>COCCOC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27])[CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole

Product 1

HCID 54296311(R)-5-bromo-3-(1-methyl-2-pyrrolidinylmethyl)-1-tosyl-1H-indoleYield 65%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of (R)-5-bromo-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole (10.0 g, 34.1 mmol) in ethyleneglycol dimethylether (50 ml) at 0° C. under a nitrogen atmosphere was added potassium hydroxide flake (9.58 g, 171 mmol) in one portion. Para-toluenesulfonyl chloride (6.83 g, 35.8 mmol) was then added portionwise to the brown slurry over a 5 min period, maintaining the temperature below 5° C. The brown slurry was then warmed to ambient temperature and stirred for a further 2 hr. The mixture was then filtered in vacuo and the filter cake washed with toluene (2×100 ml). The filtrate was then concentrated in vacuo to approximately 20 ml volume which resulted in precipitation of a cream solid. After stirring for 2 hr, the solid was filtered and dried in vacuo at 50° C. for 12 hr to give the title compound (9.91 g, 65%) as a beige solid. m.p. 98-104° C.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. filtrationThe mixture was then filtered in vacuo
  3. washthe filter cake washed with toluene (2×100 ml)
  4. concentrationThe filtrate was then concentrated in vacuo to approximately 20 ml volume which
  5. customresulted in precipitation of a cream solid
  6. stirringAfter stirring for 2 hr
  7. filtrationthe solid was filtered
  8. customdried in vacuo at 50° C. for 12 hr

Sources & evidence

ORD record
ord-dc111b5048b04026b5e1f9a5c231ae60
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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