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

HRID 929789
Notes
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Reaction equation

HRID 929789 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+].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([CH3:33])(=[O:32])=[O:31]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:33][S:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][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)(=[O:31])=[O:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 189224741-(Bromomethyl)-2-methanesulfonylbenzeneHCID 1364912503-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide2×

Product 1

HCID 762807983-[4-(2-Methanesulfonyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amideYield 3.3%

Reagents, catalysts & solvents 2

HCID 67553
Tetrabutylammonium Iodide
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

3-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 2; 50 mg, 0.245 mmol) was dissolved in DMF (1.5 mL). K2CO3 (42 mg, 0.30 mmol), tetrabutylammonium iodide (14 mg, 0.038 mmol), and 1-bromomethyl-2-methylsulfonyl-benzene (which is available from Combi-Blocks; 62 mg, 0.25 mmol) were added. The reaction mixture was heated at 40° C. for 13 h. The reaction mixture was cooled to room temperature and partitioned between H2O (5 mL) and EtOAc (5 mL). The organic layer was dried (Na2SO4), filtered, evaporated, and purified twice by chromatography (40-60% EtOAc/hexanes) to give 3-[4-(2-methanesulfonyl-benzyloxy)-phenyl]-isoxazole-5-carboxylic acid amide (3 mg, 3%) as a white powder. HRMS Calcd. for C18H17N2O5S (M+H)+, 373.0853. Found: 373.0854.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between H2O (5 mL) and EtOAc (5 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified twice by chromatography (40-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e3fc7104554e46f89e32614ad9c30756
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296711B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes