Water → HCID 86654259, compound

HRID 42140Notes

Reaction equation

HRID 42140 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O-:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[K+].Br[CH2:14][C:15]1[N:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1.O>CN(C)C=O>[Cl:21][C:18]1[N:17]=[N:16][C:15]([CH2:14][O:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 230809253-(Bromomethyl)-6-chloropyridazineHCID 67083038Potassium 4-(methanesulfonyl)phenolate

Product 1

HCID 86654259HCID 86654259, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of potassium 4-(methanesulfonyl)phenolate (150 mg, 0.713 mmol) in N,N-dimethylformamide (2 mL) was added a solution of 3-bromomethyl-6-chloropyridazine (221 mg, 1.07 mmol) in N,N-dimethylformamide (2 mL). The mixture was stirred at room temperature for 2.5 hours, poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→2/3) to give the title compound as a white crystal (148 mg, yield 69%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→2/3)

Sources & evidence

ORD record
ord-4c43a6082bd842599a6797c0af723234
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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