Pyrazole → 3-(2-(1H-Pyrazol-1-yl)ethyl)-5-fluoro-1H-indole

HRID 1095521Notes

Reaction equation

HRID 1095521 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][CH: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][CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 81531DiisopropylethylamineHCID 112072263-(2-bromoethyl)-5-fluoro-1H-indole

Product 1

HCID 574751413-(2-(1H-Pyrazol-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), pyrazole (2.04 g, 30 mmol) and ethyl-diisopropylamine (5.1 ml, 30 mmol) in abs. chloroform (80 ml) was stirred at 90° C. for 12 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 CHCl3/MeOH (20:1).

Workup

  1. washThe reaction solution was then washed twice with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated i
  4. customand the residue which remained was purified by flash chromatography with CHCl3/MeOH (20:1)

Sources & evidence

ORD record
ord-adbfa63c80a042baaa0acbdb07715642
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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