1,4-Dibromobutane → 1-(4-bromobutyl)-2-tosyl-1H-indole

HRID 574609Notes

Reaction equation

HRID 574609 reaction equation
[S:1]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Br:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.[OH-].[K+]>CN(C=O)C>[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:11]1[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 14797Potassium HydroxideHCID 118325062-tosyl-1H-indole

Product 1

HCID 152619961-(4-bromobutyl)-2-tosyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-tosyl-1H-indole (199 mg, 0.73 mmol) in 3 mL DMF was added 1,4-dibromobutane (263 μL, 2.20 mmol) in 1 mL DMF and KOH (41 mg, 0.73 mmol), and the reaction stirred at room temperature 1.75 h. The reaction mixture was then partitioned between water and ether, and the aqueous layer extracted twice with ether. The combined organic extract was washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 15% ethyl acetate in hexanes to give a final yield of 178 mg (0.44 mmol). 1H NMR (500 MHz, CDCl3, δ): 1.66-1.81 (m, 2H), 1.81-1.94 (m, 2H), 2.44 (s, 3H), 3.34 (t, J=6.4 Hz, 2H), 4.35 (t, J=7.6 Hz, 2H), 7.21 (t, J=7.0 Hz, 1H), 7.30-7.44 (m, 5H), 7.73 (d, J=7.9 Hz, 1H), 7.87 (d, J=8.1 Hz, 2H). 13C NMR (500 MHz, CDCl3, δ): 22.07, 29.04, 30.26, 33.26, 44.41, 111.08, 111.49, 121.67, 123.42, 125.83, 126.19, 128.09, 130.44, 135.22, 138.78, 139.12, 145.08. MS m/z 406.3 [M+H]+.

Workup

  1. customThe reaction mixture was then partitioned between water and ether
  2. extractionthe aqueous layer extracted twice with ether
  3. extractionThe combined organic extract
  4. washwas washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified via silica gel chromatography
  9. customto give a final yield of 178 mg (0.44 mmol)

Sources & evidence

ORD record
ord-bcbcf4346273411d8e15af41cc807709
Source dataset
uspto-grants-2015_05
Patent number
US09034895B2

Reaction notes

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