o-Xylyl bromide → HCID 76284362, compound

HRID 929776Notes

Reaction equation

HRID 929776 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:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH3:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][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 6992o-Xylyl bromideHCID 11430Potassium CarbonateHCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide2×

Product 1

HCID 76284362HCID 76284362, compoundYield 28.2%

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). 2-Methylbenzyl bromide (38 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-(2-methyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (20.9 mg, 28%). HRMS Calcd. for C18H17N2O3 (M+H)+, 309.1234. Found: 309.1233.

Workup

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

Sources & evidence

ORD record
ord-ef05760a53a447008ba85b979c40ef97
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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