1,2-Dimethoxyethane → N-(4-(6-chloropyridazin-3-yl)phenyl)methanesulfonamide

HRID 406421Notes

Reaction equation

HRID 406421 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][S:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)(=[O:12])=[O:11].C([O-])([O-])=O.[Na+].[Na+].COCCOC>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][S:10]([CH3:9])(=[O:11])=[O:12])=[CH:19][CH:18]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 2773537(4-Methanesulfonamidophenyl)boronic acid

Product 1

HCID 86650228N-(4-(6-chloropyridazin-3-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 3,6-dichloropyridazine (20.1 mmole), 4-(methylsulfonylamino)phenylboronic acid (20.1 mmole), tetrakis(triphenylphosphine)palladium (1.00 mmole), 2M Na2CO3 (30 mL), and 1,2-dimethoxyethane (120 mL). The resulting reaction mixture was heated at 85 C for 22 hours. The reaction mixture was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water. The organic extract was dried over Na2SO4 and evaporated in vacuo. The crude residue was purified by biotage column chromatography eluting with 4:1 ethyl acetate to hexane mixture to afford N-(4-(6-chloropyridazin-3-yl)phenyl)methanesulfonamide.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated at 85 C for 22 hours
  3. filtrationfiltered through celite
  4. washThe filtrate was washed with water
  5. extractionThe organic extract
  6. dry with materialwas dried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude residue was purified by biotage column chromatography
  9. washeluting with 4:1 ethyl acetate to hexane mixture

Sources & evidence

ORD record
ord-e6ad325311fc4184a13105f3c7727087
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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