Cesium carbonate → HCID 67958335, compound

HRID 536162Notes

Reaction equation

HRID 536162 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]Br)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[OH:22][C:23]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:29][C:27]3[CH:26]=[CH:25][NH:24][C:23](=[O:22])[CH:28]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 679605494-(2-Bromoethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl etherHCID 178516518HCID 178516518, compound

Product 1

HCID 67958335HCID 67958335, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2-bromoethyl)phenyl 4-Chloro-3-(trifluoromethyl)phenyl ether (335 mg, 0.883 mmol), 2,4-dihydroxypyridine (200 mg, 1.800 mmol), and cesium Carbonate (600 mg, 1.842 mmol) in N,N-dimethylformamide (DMF) (10 mL) was stirred at 120° C. for 4 h, then cooled to rt, Purification via Biotage-C18 system afforded the title product (60 mg) as a white solid.

Workup

  1. customPurification via Biotage-C18 system

Sources & evidence

ORD record
ord-0070f86bd4d44649968c310c8aa6ff57
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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