Water → HCID 58755337, compound

HRID 2251328Notes

Reaction equation

HRID 2251328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([C:26]3[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=3)[C:29]([O:31][CH3:32])=[O:30])(=[O:25])=[O:24])=[C:18]([CH3:36])[CH:17]=2)=[C:12]([CH:37]([CH3:39])[CH3:38])[O:11][N:10]=1.[C:40](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C)C=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH3:40])[S:23]([C:26]3[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=3)[C:29]([O:31][CH3:32])=[O:30])(=[O:24])=[O:25])=[C:18]([CH3:36])[CH:17]=2)=[C:12]([CH:37]([CH3:39])[CH3:38])[O:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58755351HCID 58755351, compound

Product 1

HCID 58755337HCID 58755337, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-{[(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)amino]sulfonyl}benzoate (32 mg, 56 μmol) in dimethylformamide (560 μL) was stirred with cesium carbonate (91 mg, 280 μmol) and methyl iodide (17.3 μL, 280 μmol) at 80° C. in a sealed vial. Water (2 mL) was added and the product was extracted with 50% ethyl acetate/hexanes. Yield=31 mg 94%) of methyl 3-{[(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)(methyl)amino]sulfonyl}benzoate.

Workup

  1. extractionthe product was extracted with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ec479cdf178e4dc489ef377d4dbbf1c7
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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