Imidazole → HCID 57475142, compound

HRID 1095522Notes

Reaction equation

HRID 1095522 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]=[CH:15]1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[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]=[CH:15]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 81531DiisopropylethylamineHCID 112072263-(2-bromoethyl)-5-fluoro-1H-indole

Product 1

HCID 57475142HCID 57475142, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(2-bromo-ethyl)-5-fluoro-1H-indole (4.84 g, 20 mmol), imidazole (1.36 g, 20 mmol) and ethyl-diisopropylamine (3.4 ml, 20 mmol) in abs. dioxane (50 ml) was stirred at 90° C. for 8 h until according to TLC educt was no longer present. The solvent was then removed i. vac., CHCl3 (100 ml) was added to the residue and the organic phase was washed twice with water. The organic phase was dried over Na2SO4 and concentrated i. vac. and the residue which remained was purified by flash chromatography with CHCl3/MeOH (9:1).

Workup

  1. customThe solvent was then removed i
  2. addition, CHCl3 (100 ml) was added to the residue
  3. washthe organic phase was washed twice with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated i
  6. customand the residue which remained was purified by flash chromatography with CHCl3/MeOH (9:1)

Sources & evidence

ORD record
ord-40147d6300734bae84455ff7280818af
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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