Potassium Carbonate → HCID 67135683, compound

HRID 1873345Notes

Reaction equation

HRID 1873345 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][OH:28]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:25][CH2:26][CH2:27][OH:28])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 24864014HCID 24864014, compound

Product 1

HCID 67135683HCID 67135683, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine prepared above is dissolved in N,N-dimethylformamide, and the solution is supplemented with potassium carbonate and 3-bromo-1-propanol and stirred at room temperature for overnight to obtain 6-bromo-2-[4′-(3″-hydroxypropoxy)phenyl]imidazo[1,2-a]pyridine. This is dissolved in pyridine, supplemented with p-toluenesulfonylchloride under an ice bath and then reacted at room temperature to obtain 6-bromo-2-[4′-(3″-p-toluenesulfonyloxypropoxy)phenyl]imidazo[1,2-a]pyridine as a target compound. The amount of the p-toluenesulfonylchloride to be used in this instance may be excessive relative to the reaction substrate, and is typically about double the reaction substrate 6-bromo-2-[4′-(3″-hydroxypropoxy)phenyl]imidazo[1,2-a]pyridine in molar ratio.

Sources & evidence

ORD record
ord-d2562be54c36431299452b379d7b4475
Source dataset
uspto-grants-2012_11
Patent number
US08303935B2

Reaction notes

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