Potassium Carbonate → HCID 67958516, compound

HRID 536160Notes

Reaction equation

HRID 536160 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]Cl)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].C(=O)([O-])[O-].[K+].[K+].[OH:27][C:28]1[CH:33]=[C:32]([OH:34])[CH:31]=[CH:30][N:29]=1>CN(C)C=O.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][O:34][C:32]3[CH:31]=[CH:30][NH:29][C:28](=[O:27])[CH:33]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl etherHCID 178516518HCID 178516518, compound

Product 1

HCID 67958516HCID 67958516, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl ether (500, mg, 1.557 mmol), potassium carbonate (500 mg, 3.62 mmol) and 2,4-dihydroxypyridine (350 mg, 3.15 mmol) in N,N-dimethylformamide (DMF) (5 mL) was heated at 60° C. for overnight, then cooled to rt and diluted with acetonitrile. Solid suspension was removed by filtration, concentrated. Purification via Biotage-C18 system afforded the title product (310 mg) as a white solid. LC-MS (ESI): m/z 396 [M+H]+; 3.48 min (ret time).

Workup

  1. customSolid suspension was removed by filtration
  2. concentrationconcentrated
  3. customPurification via Biotage-C18 system

Sources & evidence

ORD record
ord-9517a6be64c4464e97409f5dbef3dc13
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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