Cesium carbonate → N-[4-(5-acetyl-6-chloro-pyrazin-2-yl)-phenyl]-2,3-dichloro-benzenesulfonamide

HRID 706775Notes

Reaction equation

HRID 706775 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[N:4][CH:5]=[C:6](Cl)[N:7]=1.[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[S:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=1)(=[O:22])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CCCCCCC.CCOC(C)=O.O>[C:9]([C:3]1[N:4]=[CH:5][C:6]([C:27]2[CH:26]=[CH:25][C:24]([NH:23][S:20]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=3[Cl:12])(=[O:21])=[O:22])=[CH:29][CH:28]=2)=[N:7][C:2]=1[Cl:1])(=[O:11])[CH3:10]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 156968511-(3,5-Dichloropyrazin-2-yl)ethan-1-oneHCID 586961462,3-dichloro-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzenesulfonamide

Product 1

HCID 86678949N-[4-(5-acetyl-6-chloro-pyrazin-2-yl)-phenyl]-2,3-dichloro-benzenesulfonamide

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
100 °C

Procedure

1-(3,5-Dichloro-pyrazin-2-yl)-ethanone (200 mg) and 2,3-dichloro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzenesulfonamide (448.3 mg), prepared as in example 1, was added to a reaction vessel containing a magnetic stirring bar together with 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (61 mg) and cesium carbonate (1.0 g), followed by 9 ml dioxane and 1 ml water, and the mixture heated to 100° C. under stirring. After 2 h the reaction mixture was cooled to RT and quenched with a saturated aqueous sodium bicarbonate solution (30 ml) and extracted with EtOAc (3×30 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated to afford the crude product as a brown oil-Purification by flash chromatography on silica gel using a mixture of EtOAc and heptane as the eluent afforded N-[4-(5-acetyl-6-chloro-pyrazin-2-yl)-phenyl]-2,3-dichloro-benzenesulfonamide as a colorless solid after evaporation of the solvents under reduced pressure. Yield: 230 mg (48%).

Workup

  1. additionwas added to a reaction vessel
  2. temperatureAfter 2 h the reaction mixture was cooled to RT
  3. customquenched with a saturated aqueous sodium bicarbonate solution (30 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product as a brown oil-Purification by flash chromatography on silica gel using

Sources & evidence

ORD record
ord-31b0825a0a5343a99cfedda808ab3ea2
Source dataset
uspto-grants-2015_11
Patent number
US09174993B2

Reaction notes

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