4-Hydroxybenzaldehyde → 4-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzaldehyde

HRID 1807448Notes

Reaction equation

HRID 1807448 reaction equation
Cl[C:2]1[S:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[S:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:10]=[C:2]1[O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 513584282-Chloro-(1,3)thiazolo(4,5-b)pyridine

Product 1

HCID 574483844-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro[1,3]thiazolo[4,5-b]pyridine (25 g, 147 mmol) in CH3CN (500 mL) was added 4-hydroxybenzaldehyde (19.8 g, 147 mmol, 1 equiv.) and K2CO3 (22.3 g, 147 mmol, 1 equiv.). The heterogeneous mixture was heated at reflux for 72 h and then cooled to rt. Purification was conducted using one of the following methods.

Workup

  1. temperatureThe heterogeneous mixture was heated
  2. temperatureat reflux for 72 h
  3. customPurification

Sources & evidence

ORD record
ord-93a1e5d647ce41a3b383d2e9da207ae0
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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