2-(Methylamino)ethanol → 2-[(5-Bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)(methyl)amino]ethanol

HRID 1626009Notes

Reaction equation

HRID 1626009 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[Br:6][C:7]1[C:8](Cl)=[C:9]2[CH:15]=[CH:14][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:10]2=[N:11][CH:12]=1>>[Br:6][C:7]1[C:8]([N:2]([CH3:1])[CH2:3][CH2:4][OH:5])=[C:9]2[CH:15]=[CH:14][N:13]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:10]2=[N:11][CH:12]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 575376665-Bromo-4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 670785912-[(5-Bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)(methyl)amino]ethanol

Conditions

Temperature
145 °C

Procedure

2-(Methylamino)ethanol (1.5 ml) was added to 5-bromo-4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine obtained by the method described in WO 2008/150914 (700 mg), and the mixture was heated under reflux at 145° C. for 18 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (472 mg).

Workup

  1. customobtained by the method
  2. temperaturethe mixture was heated
  3. temperatureThe reaction solution was cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-0d41178b1d0a4ccb8d956106a37a5c52
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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