Diisopropylethylamine → 3-(2-(1H-1,2,3-Triazol-1-yl)ethyl)-5-fluoro-1H-indole

HRID 1095514Notes

Reaction equation

HRID 1095514 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:13])[CH:11]=2)[NH:6][CH:5]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[N:15]1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[N:14]1([CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:13])[CH:11]=3)[NH:6][CH:5]=2)[CH:18]=[CH:17][N:16]=[N:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112072263-(2-bromoethyl)-5-fluoro-1H-indoleHCID 178418936HCID 178418936, compound

Product 1

HCID 574751383-(2-(1H-1,2,3-Triazol-1-yl)ethyl)-5-fluoro-1H-indole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-(2-bromo-ethyl)-5-fluoro-1H-indole (7.26 g, 30 mmol), 1,2,3-triazole (2.07 g, 30 mmol) and ethyl-diisopropylamine (5.1 ml, 30 mmol) in abs. chloroform (70 ml) was boiled under reflux for 24 h. The reaction solution was then washed twice with water, dried over Na2SO4 and concentrated i. vac. and the residue which remained was purified by flash chromatography with EA/cyclohexane (1:1→4:1).).

Workup

  1. temperatureunder reflux for 24 h
  2. washThe reaction solution was then washed twice with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated i
  5. customand the residue which remained was purified by flash chromatography with EA/cyclohexane (1:1→4:1)

Sources & evidence

ORD record
ord-7e91131777cc46caab60710ed4e1658c
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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