4-Toluenesulfonyl chloride → 3-iodo-5-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indole

HRID 1529310Notes

Reaction equation

HRID 1529310 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:16]=[N:15][CH:14]=[C:13]([O:17][CH:18]([CH3:20])[CH3:19])[N:12]=3)[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:16]=[N:15][CH:14]=[C:13]([O:17][CH:18]([CH3:20])[CH3:19])[N:12]=3)[CH:9]=2)[N:4]([S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 679599583-iodo-5-(6-isopropoxypyrazin-2-yl)-1H-indole

Product 1

HCID 679596923-iodo-5-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indoleYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-5-(6-isopropoxy-pyrazin-2-yl)-1H-indole (20 g, 0.053 mol) in DMF (200 mL) was added NaH (6.5 g, 0.158 mol) slowly at 0° C., and then stirred for 15 min. p-Toluenesulfonyl chloride (15.10 g, 0.079 mol) was added slowly to the reaction mixture and stirred for 1 h. The resulting mixture was poured into ice with stirring and the precipitate was formed. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to give the crude product. The crude product was purified by column chromatography eluting with EtOAc and n-hexane to afford the desire 3-iodo-5-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indole (15.5 g, 55%) as pale brown solid. MS (ESI, m/z): 533.6 (M+1).

Workup

  1. additionwas added slowly to the reaction mixture
  2. additionThe resulting mixture was poured into ice
  3. stirringwith stirring
  4. customthe precipitate was formed
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried under vacuum
  8. customto give the crude product
  9. customThe crude product was purified by column chromatography
  10. washeluting with EtOAc and n-hexane

Sources & evidence

ORD record
ord-964dc23de72d4de3842a13df28742727
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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