Potassium Carbonate → HCID 76284629, compound

HRID 929784Notes

Reaction equation

HRID 929784 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:17]=[C:16]([C:18]([NH2:20])=[O:19])[O:15][N:14]=2)=[CH:9][CH:8]=1)(C)(C)C.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[F-].[K+].[F:49][C:50]([F:60])([F:59])[C:51]1[CH:52]=[C:53]([CH:56]=[CH:57][CH:58]=1)[CH2:54]Cl>CN(C=O)C.O>[F:49][C:50]([F:59])([F:60])[C:51]1[CH:52]=[C:53]([CH:56]=[CH:57][CH:58]=1)[CH2:54][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:17]=[C:16]([C:18]([NH2:20])=[O:19])[O:15][N:14]=2)=[CH:11][CH:12]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 697163-(Trifluoromethyl)benzyl chlorideHCID 522689Potassium FluorideHCID 90202338HCID 90202338, compound2×

Product 1

HCID 76284629HCID 76284629, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 13; 40 mg, 0.126 mmol) was dissolved in DMF (1.5 mL). K2CO3 (19 mg, 0.14 mmol), 18-crown-6 (6 mg, 0.02 mmol), KF (8 mg, 0.14 mmol), and 3-(trifluoromethyl)benzyl chloride (20 μL, 0.129 mmol) were added. The reaction mixture was stirred at room temperature for 10 min and then at 40° C. for 12 h. H2O (2.5 mL) was added and the mixture was extracted with EtOAc. The organic layer was evaporated to give 3-[4-(3-trifluoromethyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (32.7 mg, 72%) as an off-white powder. HRMS Calcd. for C18H13F3N2O3 (M+), 362.0878. Found: 362.0872.

Workup

  1. waitat 40° C. for 12 h
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-ad6673a95f0f4abdb68c6f1e24975827
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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