o-Xylyl bromide → N-(3-(2-methylbenzyloxy)-4-chlorophenyl)thiazol-2-amine

HRID 1474001Notes

Reaction equation

HRID 1474001 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+].[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Br>CC(C)=O>[CH3:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][O:14][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6992o-Xylyl bromideHCID 10796Cesium carbonateHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 86645045N-(3-(2-methylbenzyloxy)-4-chlorophenyl)thiazol-2-amineYield 58%

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 (50 mg, 0.22 mmol) and Cs2CO3 (72 mg, 0.22 mmol) in acetone (4.4 mL) was treated with 2-methylbenzyl bromide (41 mg, 0.22 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 4/1) in 58% yield (42 mg).

Workup

  1. customReaction control by TLC
  2. customafter 3 h

Sources & evidence

ORD record
ord-3a00c407a5a14c7ea98ad4fc1851a765
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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