Potassium Carbonate → 2-((5-Bromo-3-morpholinopyridin-2-yl)oxy)ethanol

HRID 594052Notes

Reaction equation

HRID 594052 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5](=[O:8])[NH:6][CH:7]=1.I[CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5](=[O:8])[N:6]([CH2:16][CH2:17][OH:18])[CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([O:8][CH2:16][CH2:17][OH:18])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 904098535-Bromo-3-morpholinopyridin-2-ol

Product 2

HCID 904079522-((5-Bromo-3-morpholinopyridin-2-yl)oxy)ethanolHCID 904085545-bromo-1-(2-hydroxyethyl)-3-morpholinopyridin-2(1H)-one

Procedure

Method 1 was followed using 5-bromo-3-morpholinopyridin-2(1H)-one (1.0 equiv.), 2-iodoethanol (1.0 equiv.) and potassium carbonate (2.0 equiv.) at room temperature to give 5-bromo-1-(2-hydroxyethyl)-3-morpholinopyridin-2(1H)-one and 2-((5-bromo-3-morpholinopyridin-2-yl)oxy)ethanol as a mixture of two isomers (˜5:1 ratio). LCMS (m/z) (M+H)=303/305, Rt=0.47 min and 0.62 min.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-d1338515b33441cca9b99a0399b6a54d
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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