Potassium Carbonate → HCID 76284625, compound

HRID 929779Notes

Reaction equation

HRID 929779 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH2:15])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25]Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:13]([NH2:15])=[O:14])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide2×

Product 1

HCID 76284625HCID 76284625, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

3-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 2; 50 mg, 0.24 mmol), K2CO3 (37 mg, 0.27 mmol) and tetrabutylammonium iodide (9 mg, 0.024 mmol) were taken up in DMF (2.4 mL). 2-Chloro-6-fluorobenzyl chloride (45 mg, 0.24 mmol) was added and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was purified by high-throughput purification to give 3-[4-(2-chloro-6-fluoro-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (12.3 mg, 15%). HRMS Calcd. for C17H13ClFN2O3 (M+H)+, 347.0593. Found: 347.0591.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by high-throughput purification

Sources & evidence

ORD record
ord-886c4337eec948339ad2adfe7a17b089
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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