2-(Dimethylamino)ethanol → 2-[(5-Bromo-2-pyridinyl)oxy]-N,N-dimethylethanamine

HRID 459852Notes

Reaction equation

HRID 459852 reaction equation
CC(C)([O-])C.[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][N:9]=1.[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][OH:19]>CN(C=O)C>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([O:19][CH2:18][CH2:17][N:16]([CH3:20])[CH3:15])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 693532,5-DibromopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 232996382-[(5-Bromo-2-pyridinyl)oxy]-N,N-dimethylethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium t-butoxide was added to a DMF solution of 2,5-dibromopyridine and 2-(dimethylamino)ethanol, and the whole was stirred at an oil bath temperature of 100° C. for 3 hours to obtain N-{2-[(5-bromopyridin-2-yl)oxy]ethyl}—N,N-dimethylamine, which was further treated in a similar manner to Reference Examples 11 and 12 to obtain an objective compound.

Sources & evidence

ORD record
ord-c54482937ad544f5aa6ea461616e30d6
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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