Potassium Carbonate → HCID 86645036, compound

HRID 1473984Notes

Reaction equation

HRID 1473984 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[CH:5][C:4]=1[OH:16].C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27]>CC(C)=O>[CH3:15][C:13]1[N:14]=[C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:16][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH:5]=2)[S:11][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 534390572-Methoxy-5-[(4-methyl-1,3-thiazol-2-yl)amino]phenol

Product 1

HCID 86645036HCID 86645036, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method A, a mixture of 2-methoxy-5-(4-methylthiazol-2-ylamino)phenol (30 mg, 0.10 mmol) and K2CO3 (15 mg, 0.11 mmol) in acetone (1.0 mL) was treated with 4-bromo-2-methyl-2-butene (0.014 mL, 0.12 mmol). The reaction mixture was heated at reflux for 4 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 54% yield (16 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h

Sources & evidence

ORD record
ord-15be69e63c464b5eb06ec591d77fa0ef
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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