Sodium Iodide → 3-{2-[3-(4-Fluorobenzoylmethyl)pyrrolidin-1-yl]ethyl}-5-methoxyindole

HRID 1941115Notes

Reaction equation

HRID 1941115 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][CH:5]=1.[F:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([CH2:22][CH:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)=[O:21])=[CH:18][CH:17]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(C(CC)=O)C>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([CH2:22][CH:23]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][C:4]3[C:12]4[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=4)[NH:6][CH:5]=3)[CH2:24]2)=[O:21])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 110850303-(4-Fluorobenzoylmethyl)pyrrolidineHCID 111078683-(2-bromoethyl)-5-methoxy-1H-indole

Product 1

HCID 110253113-{2-[3-(4-Fluorobenzoylmethyl)pyrrolidin-1-yl]ethyl}-5-methoxyindole

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

A mixture of 5 g (0.0197 mol) of the product obtained in Stage 2, 4 g (0.0216 mol) of 3-(4-fluorobenzoylmethyl)pyrrolidine, 0.1 g of sodium iodide and 3 g of potassium carbonate in 100 ml of diethyl ketone is brought to reflux for 24 hours. The inorganic salts are then filtered off, the solvent is evaporated under vacuum, the residue is taken up in 100 ml of dichloromethane and this organic phase is washed with 100 ml of water. After drying over magnesium sulfate and evaporation of the solvent, the residue is purified by chromatography on a silica column, Merck 70-230 mesh, using a dichloromethane/methanol/aqueous ammonia (97/3/0.3) mix-ture as eluent.

Workup

  1. temperatureto reflux for 24 hours
  2. filtrationThe inorganic salts are then filtered off
  3. customthe solvent is evaporated under vacuum
  4. washthis organic phase is washed with 100 ml of water
  5. dry with materialAfter drying over magnesium sulfate and evaporation of the solvent
  6. customthe residue is purified by chromatography on a silica column, Merck 70-230 mesh
  7. additionmix-ture as eluent

Sources & evidence

ORD record
ord-276f29dcfd074555b2a01e5aa0cb3d5f
Source dataset
uspto-grants-1997_12
Patent number
US05703070

Reaction notes

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