Styrene Oxide → 2-{[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]amino}-2-phenylethanol

HRID 506837Notes

Reaction equation

HRID 506837 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:34][CH3:35].[CH2:36]1[O:44][CH:37]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([C:13]3[N:23]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH:22][CH:37]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH2:36][OH:44])=[C:15]4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:34][CH3:35]

Participants

4

Reactant 2

HCID 7276Styrene OxideHCID 68468798HCID 68468798, compound

Product 1

HCID 684694462-{[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]amino}-2-phenylethanolYield 7.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.09 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methylamine in 20 cm3 of ethanol, at a temperature in the region of 20° C., is added 0.022 g of styrene oxide. The reaction medium is refluxed for five days. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is purified by flash-pack column chromatography (SiO2, dichloromethane/methanol 95/05 by volume as eluents) to give 0.008 g of 2-{[2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl]amino}-2-phenylethanol with the following characteristics:

Workup

  1. temperatureThe reaction medium is refluxed for five days
  2. temperatureAfter cooling
  3. concentrationthe reaction medium is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by flash-pack column chromatography (SiO2, dichloromethane/methanol 95/05 by volume as eluents)

Sources & evidence

ORD record
ord-7332c3eb7d0c4270a1ef1f8e53e0e94e
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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