Cesium carbonate → HCID 15956106, compound

HRID 1473997Notes

Reaction equation

HRID 1473997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[OH:14].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[O:14][CH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 151114782-(Bromomethyl)thiazoleHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 15956106HCID 15956106, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method B, a mixture of 2-chloro-5-(thiazol-2-ylamino)phenol (100 mg, 0.44 mmol) and Cs2CO3 (147 mg, 0.44 mmol) in acetone (4.4 mL) was treated with 2-bromomethylthiazole (88 mg, 0.44 mmol) at RT. Reaction control by TLC showed full conversion after 3 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 1/1) in 33% yield (47 mg).

Workup

  1. customReaction control by TLC
  2. customafter 3 h

Sources & evidence

ORD record
ord-8b4654c847c14007ab3938aac854997d
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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