Ethyl Acetate → HCID 67072706, compound

HRID 386553Notes

Reaction equation

HRID 386553 reaction equation
Cl[C:2]1[C:7](C2C=CC=CC=2)=[N:6][NH:5][C:4](=[O:14])[CH:3]=1.[C:15]([O-])([O-])=[O:16].[K+].[K+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH3:15][O:16][C:2]1[CH:7]=[N:6][N:5]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:4](=[O:14])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 27358035-Chloro-6-phenylpyridazin-3(2H)-one

Product 1

HCID 67072706HCID 67072706, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring solution of 5-chloro-6-phenylpyridazin-3(2H)-one (78 mg, 0.618 mmol) in DMF (3 mL) at room temperature under argon was added K2CO3 (256 mg, 1.855 mmol), and was followed by addition of 1-(bromomethyl)-4-methoxybenzene (149 mg, 0.742 mmol). The resulting reaction mixture was stirred at room temperature overnight. EtOAc (20 mL) and brine (30 mL) were added to the reaction mixture. Layers were separated. Organic layer were washed with water (15 mL), and brine (15 mL). Organic phase was dried (MgSO4), filtered and concentrated. Crude product (117 mg) (MS (ESI) 247 (M+H)) was used directly to next step.

Workup

  1. customThe resulting reaction mixture
  2. customLayers were separated
  3. washOrganic layer were washed with water (15 mL), and brine (15 mL)
  4. dry with materialOrganic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2ddd7232a5654c34a71000a89eb967de
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Reaction notes

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