Potassium Carbonate → HCID 86645039, compound

HRID 1473987Notes

Reaction equation

HRID 1473987 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([O-])([O-])=O.[K+].[K+].Br[CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31]>CC(C)=O>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=2)=[CH:3][C:2]=1[O:1][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 53438568Ethyl 2-(3-hydroxy-4-methoxyanilino)-1,3-thiazole-4-carboxylate

Product 1

HCID 86645039HCID 86645039, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method A, a mixture of ethyl 2-(3-hydroxy-4-methoxyphenylamino)thiazole-4-carboxylate (139 mg, 0.47 mmol) and K2CO3 (72 mg, 0.52 mmol) in acetone (4.7 mL) was treated with 4-bromo-2-methyl-2-butene (0.066 mL, 0.56 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 42% yield (71 mg).

Workup

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

Sources & evidence

ORD record
ord-069488ed62dc4edc89f0038d37da5eb7
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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