Water → HCID 21922816, compound

HRID 1245000Notes

Reaction equation

HRID 1245000 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][CH2:19]OS(C3C=CC(C)=CC=3)(=O)=O)[C:13]=2[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:8][CH:7]=1.O>CS(C)=O>[N:1]([CH2:19][CH2:18][CH2:17][N:14]1[CH:15]=[CH:16][C:12]([C:9]2[CH:8]=[CH:7][C:6]([F:5])=[CH:11][CH:10]=2)=[C:13]1[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 21922598HCID 21922598, compound

Product 1

HCID 21922816HCID 21922816, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

0.38 g (5.90 mmol) of sodium azide were added to a solution of 1.33 g (2.95 mmol) of 3-(4-fluorophenyl)-2-(pyridin-4-yl)-1-[3-(p-toluenesulfonyloxy)propyl]-1H-pyrrole [prepared as described in step 22(iii) above] in 13 ml of dimethylsulfoxide. The resulting mixture was stirred at 70° C. for 1 hour. At the end of this time water was added to the reaction mixture and then this was extracted with dichloromethane. The organic extract was washed with water and then concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 1:1 by volume mixture of hexane and ethylacetate as the eluant to afford 100 mg (yield 11%) of the title compound as a pale brown powder.

Workup

  1. extractionthis was extracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by chromatography on a silica gel column
  7. additionby volume mixture of hexane and ethylacetate as the eluant

Sources & evidence

ORD record
ord-e8ee1d57ca934c96a30d9b7a22e15b91
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

Loading…