Ethyl Acetate → N-[3-fluoro-5-(pyridin-3-yloxy)phenyl]-2-(hydroxymethyl)benzenesulfonamide

HRID 1809830Notes

Reaction equation

HRID 1809830 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]1[CH:13]=[C:14]([NH:25][S:26]([C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31](OC)=[O:32])(=[O:28])=[O:27])[CH:15]=[C:16]([O:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)(=O)C>O1CCCC1>[F:11][C:12]1[CH:13]=[C:14]([NH:25][S:26]([C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[CH2:31][OH:32])(=[O:28])=[O:27])[CH:15]=[C:16]([O:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 67133780Methyl 2-({[3-fluoro-5-(pyridin-3-yloxy)phenyl]amino}sulfonyl)benzoate

Product 1

HCID 67133536N-[3-fluoro-5-(pyridin-3-yloxy)phenyl]-2-(hydroxymethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0M diisobutylaluminum hydride in tetrahydrofuran (7.50 ml) was added to a solution of methyl 2-({[3-fluoro-5-(pyridin-3-yloxy)phenyl]amino}sulfonyl)benzoate (1.50 g) in tetrahydrofuran (22 ml) at 0° C., and the reaction solution was stirred at the same temperature for 1 hour. A saturated aqueous solution of Rochelle salt and ethyl acetate were added to the reaction solution, and the mixture was stirred for 30 minutes, followed by being extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel chromatography to yield the title compound as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionby being extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6865bea689194505b3617507fe8e4120
Source dataset
uspto-grants-2013_01
Patent number
US08362052B2

Reaction notes

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