Potassium Carbonate → 3-[4-(2-Cyano-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide

HRID 929772Notes

Reaction equation

HRID 929772 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+].[C:22]([C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br)#[N:23]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:22]([C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[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)#[N:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide2×

Product 1

HCID 762843583-[4-(2-Cyano-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amideYield 27%

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-Cyanobenzyl bromide (53 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-cyano-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (20.7 mg, 27%). LRMS (ESI+): m/z [M+CH3CN+H]+ 361.1.

Workup

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

Sources & evidence

ORD record
ord-1160c5f5f61c410a902e468c3458ffa0
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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