Sodium Iodide → HCID 67717294, compound

HRID 1683870Notes

Reaction equation

HRID 1683870 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][NH:19]1)(=[O:5])=[O:4])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36]Cl.[I-].[Na+]>CN(C)C=O>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][C@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 22873790HCID 22873790, compound

Product 1

HCID 67717294HCID 67717294, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 5-(2-ethylsulphonylethyl)-3-(2(R)-pyrrolidinylmethyl)-1H-indole (Preparation 5; 150 mg, 0.47 mmol) in dry dimethylformamide (4 ml) at room temperature under nitrogen were added, sequentially, anhydrous sodium carbonate (110 mg, 1.04 mmol), 2-pyridylmethyl chloride hydrochloride (85 mg, 0.52 mmol) and sodium iodide (10 mg). The resulting mixture was heated at 100° C. for 18 hours, then allowed to cool to room temperature. It was then partitioned between ethyl acetate and water, and the organic phase separated, washed with water (3×), dried (Na2SO4), and evaporated under reduced pressure to give an oil. Purification by column chromatography on silica gel, eluting with an ethanol in dichloromethane gradient (0 to 5% ethanol), afforded the title compound as a gum (62 mg). [α]D25 +22° (c=0.1, CH3OH). Found: C,59.89; H,6.44; N,9.07. C23H29N3O2S; 0.75 CH2Cl2 requires C,60.02; H,6.47; N,8.84%. δCDCl3): 1.35(3H,t), 1.50-1.90(4H,m), 2.30-2.40(1H,m), 2.65-2.75(1H,m), 2.90(3H,q and m), 3.00-3.20(2H,m), 3.20-3.30(4H,m), 3.60(1H,d), 4.28(1H,d), 5.30(1.5H,s,CH2Cl2), 7.02(1H,d), 7.05(1H,s), 7.16-7.20(1H,dd), 7.30(1H,d), 7.40(1H,s), 7.50(1H,d), 7.70(1H,dd), 8.14(1H,br s), 8.58(1H,d).

Workup

  1. temperatureto cool to room temperature
  2. customIt was then partitioned between ethyl acetate and water
  3. customthe organic phase separated
  4. washwashed with water (3×)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customPurification by column chromatography on silica gel
  9. washeluting with an ethanol in dichloromethane gradient (0 to 5% ethanol)

Sources & evidence

ORD record
ord-4ffdce1444604ef480e7d149d0e95952
Source dataset
uspto-grants-1997_06
Patent number
US05639779

Reaction notes

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