Benzene → 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole

HRID 1657323Notes

Reaction equation

HRID 1657323 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[NH2:20][CH:21]([C:23]1[N:24]=[CH:25][N:26]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]=1[CH3:28])[CH3:22].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH:56]1C=CC=C[CH:57]=1>O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:3]=1[CH2:56][CH2:57][NH:20][CH:21]([C:23]1[N:24]=[CH:25][N:26]([C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:27]=1[CH3:28])[CH3:22]

Participants

7

Reactant 5

HCID 241BenzeneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 104066724-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazoleHCID 105727373-methyl-1-(phenylsulfonyl)-1H-indole

Product 1

HCID 102588713-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[2-methanesulfonyloxy)ethyl]-3-methyl-1-(benzenesulfonyl)indole (4.32 g), (-)-4-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazole (3.67 g), sodium iodide (456 mg) and potassium carbonate [1.51 g) in benzene (43 ml) was stirred at reflux for 24 hours. The reaction mixture was diluted with cold water and extracted twice with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (eluted with 5% methanol in chloroform) to give (-)-3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-(benzenesulfonyl)indole (4.82 g) as amorphous powder.

Workup

  1. temperatureat reflux for 24 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (eluted with 5% methanol in chloroform)

Sources & evidence

ORD record
ord-8311d7f5771846edbb7f073ba33ccab5
Source dataset
uspto-grants-1993_10
Patent number
US05256780

Reaction notes

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