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

HRID 2088974Notes

Reaction equation

HRID 2088974 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-4b71473d42b04c8d9bbb88eff4383534
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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