Sodium Iodide → HCID 22859588, compound

HRID 1441079Notes

Reaction equation

HRID 1441079 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[CH:17]1([CH2:20]Br)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>COCCOC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH2:20][CH:17]1[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81503BromomethylcyclopropaneHCID 228595901H-Indole, 5-bromo-3-(2-pyrrolidinylmethyl)-, (R)-

Product 1

HCID 22859588HCID 22859588, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5-Bromo-3-(pyrrolidin-2(R)-ylmethyl)-1H-indole (1.84 g, 6.3 mmol) (see Preparation 55), cyclopropylmethyl bromide (0.67 ml, 6.9 mmol), sodium carbonate (0.73 g, 6.9 mmol) and sodium iodide (1.0 g, 6.7 mmol) in 1,2-dimethoxyethane (10 ml) was refluxed under nitrogen for 14 hours. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate and aqueous sodium carbonate. The organic phase was washed with more aqueous sodium carbonate, dried (Na2SO4) and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide (90:10:0.05) to yield the title compound as a foam (2.09 g). Found: C,61.22; H,6.40; N,8.39. C17H21BrN2 requires: C,61.26; H,6.35; N,8.41%.

Workup

  1. customwas partitioned between ethyl acetate and aqueous sodium carbonate
  2. washThe organic phase was washed with more aqueous sodium carbonate
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with dichloromethane/methanol/ammonium hydroxide (90:10:0.05)

Sources & evidence

ORD record
ord-72d030a502ba4c15b38b933ac846ce5b
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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