Sodium hydride → HCID 57987621, compound

HRID 1869801Notes

Reaction equation

HRID 1869801 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH:20]([OH:25])[C:21]([O:23][CH3:24])=[O:22])[CH:15]=2)[N:10]=1.Br[CH2:27][C:28]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35].[H-].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:34][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:35])[C:28]=1[CH2:27][O:25][CH:20]([CH2:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH:18]=[CH:17]2)[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 516892Sodium BicarbonateHCID 57987619HCID 57987619, compound

Product 1

HCID 57987621HCID 57987621, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-[2-(2,6-dichlorophenyl)-6-quinolinyl]-2-hydroxypropanoate 55 (0.159 g) and α-bromo-2,6-dichlorotoluene (1.05 g) in DMF (3.5 ml) is added 17 mg of NaH (60% dispersion in mineral oil) and Ag2O (0.102 g). The solution is stirred for 1 night at room temperature. A saturated solution of NaHCO3 is added. The aqueous phase is extracted with AcOEt (3×10 ml). The organic phases are washed with water (2×10 ml), with brine and dried over MgSO4. After concentration, the residue is purified twice over silica gel using AcOEt/petroleum ether 10/90 then 15/85 as eluent to give methyl 2-[(2,6-dichlorobenzyl)oxy]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 56.

Workup

  1. extractionThe aqueous phase is extracted with AcOEt (3×10 ml)
  2. washThe organic phases are washed with water (2×10 ml), with brine
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration
  5. customthe residue is purified twice over silica gel

Sources & evidence

ORD record
ord-f92ef68c5cb14da6b937b7a8ca8c6347
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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