Sodium hydride → HCID 178470053, compound

HRID 1497089Notes

Reaction equation

HRID 1497089 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:27])[CH2:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[C:18]#[C:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])=[O:9])[CH3:4]>CS(C)=O.C(OCC)(=O)C>[CH2:3]([O:5][C:6]([C:7]1[C:8]([OH:9])=[N:10][C:11]2[C:12]([C:18]=1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[O:27])[CH3:4]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 86682949HCID 86682949, compound

Product 1

HCID 178470053HCID 178470053, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of sodium hydride (60%; 32 mg, 0.8 mmol) in DMSO (3 ml) was added a solution of N-[4-chloro-2-(2-chloro-phenylethynyl)-phenyl]-malonamic acid ethyl ester (200 mg, 0.532 mmol) in DMSO (2 ml) under nitrogen at 25° C., and the reaction mixture was stirred for 2 h at 80° C. The reaction mixture was diluted with ethyl acetate (15 ml), and the organic layer was washed with brine (3×10 ml), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (20% EtOAc in hexane) to afford 6-chloro-4-(2-chloro-benzyl)-2-hydroxy-quinoline-3-carboxylic acid ethyl ester (63 mg, 32%) as an off white solid. LC-MS (ESI): 376 (M+H)+.

Workup

  1. washthe organic layer was washed with brine (3×10 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude residue which
  6. customwas purified by flash column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-9a15032c9c704d72b46ef2cd469387ee
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…