Potassium Carbonate → 3-[4-(3,4-Dimethyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide

HRID 929771Notes

Reaction equation

HRID 929771 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+].[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[CH3:31])[CH2:26]Br>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[CH3:31])[CH2:26][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 131991903,4-Dimethylbenzyl bromideHCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide2×

Product 1

HCID 902024753-[4-(3,4-Dimethyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amideYield 11.2%

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). 3,4-Dimethylbenzyl bromide (77 mg, 0.27 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-(3,4-dimethyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (8.7 mg, 11%). LRMS (ESI+): m/z [M+H+CH3CN]+ 364.2.

Workup

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

Sources & evidence

ORD record
ord-3dd143a72c534e68a75dda7b2ad5df28
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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