Tyrosol → HCID 86666209, compound

HRID 705900Notes

Reaction equation

HRID 705900 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Cl:11][C:12]1[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:11][C:12]1[N:13]=[N:14][C:15]([O:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 10393TyrosolHCID 11430Potassium CarbonateHCID 673313,6-Dichloropyridazine

Product 1

HCID 86666209HCID 86666209, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-(2-hydroxyethyl)phenol (1.533 g, 11.09 mmol) in DMF (15 mL) was added 3,6-dichloropyridazine (1.574 g, 10.57 mmol) and K2CO3 (1.752 g, 12.68 mmol). The mixture was heated at 110° C. overnight. Purification via reverse phase flash chromatography then afforded the title compound (1.5 g, 5.98 mmol, 56.6% yield). LCMS: rt=2.23 min, [M+H+]=251

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-c23af3c2a6094aa7872058e65e562bcd
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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