Sodium hydride → (3-(((2-(3-Chloro-phenoxy)-ethyl)-(Pyridine-3-sulfonyl)-amino)-methyl)-phenyl)-acetic acid methyl ester

HRID 2300417Notes

Reaction equation

HRID 2300417 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:24])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][NH:14][S:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:8]=1.Br[CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1>CN(C=O)C>[CH3:3][O:4][C:5](=[O:24])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]([CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)[S:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25077201-(2-Bromoethoxy)-3-chlorobenzeneHCID 54480791{3-[(Pyridine-3-sulfonylamino)-methyl]-phenyl}acetic acid methyl ester

Product 1

HCID 53728724(3-(((2-(3-Chloro-phenoxy)-ethyl)-(Pyridine-3-sulfonyl)-amino)-methyl)-phenyl)-acetic acid methyl esterYield 15.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium hydride (60% in mineral oil, 0.016 g, 0.3996 mmol) in 2 mL DMF was added (3-((pyridine-3-sulfonylamino)-methyl)-phenyl)-acetic acid methyl ester (from Preparation 14, 0.096 g, 0.333 mmol) at 0° C. and the reaction was stirred at room temperature for 30 minutes. After cooling to 0° C., 1-(2-bromo-ethoxy)-3-chloro-benzene (from Preparation 29, 0.094 g, 0.399 mmol) was added and the reaction was stirred at room temperature overnight. The DMF was removed in vacuo. The residue was diluted with EtOAc and the organic solution was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica gel (0.5% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2) to afford the title compound of Step A (0.025 g). MS 475 (M+1).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe reaction was stirred at room temperature overnight
  3. customThe DMF was removed in vacuo
  4. additionThe residue was diluted with EtOAc
  5. washthe organic solution was washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product was purified by flash chromatography on silica gel (0.5% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2dadc70d37da40e2bdddc516fb0323c2
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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