4-amino-N-methylbenzene-1-sulfonamide → HCID 11668042, compound

HRID 1437748Notes

Reaction equation

HRID 1437748 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:14])[N:3]=1.CC(C)([O-])C.[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH2:67][C:68]1[CH:73]=[CH:72][C:71]([S:74]([NH:77][CH3:78])(=[O:76])=[O:75])=[CH:70][CH:69]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:14][C:4]1[N:3]=[C:2]([NH:67][C:68]2[CH:73]=[CH:72][C:71]([S:74]([NH:77][CH3:78])(=[O:76])=[O:75])=[CH:70][CH:69]=2)[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=1

Participants

8

Reactant 4

HCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 634876Binap, (A+-)-HCID 11715586HCID 11715586, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11668042HCID 11668042, compoundYield 35.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2′,6′-dichloro-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl (500 mg, 2.15 mmol) in toluene (6 mL) were added potassium tert-butoxide (486 mg, 4.3 mmol), palladium(II) acetate (24 mg, 0.1 mmol), BINAP (67 mg, 0.1 mmol), and 4-amino-N-methylbenzenesulfonamide (444 mg, 2.15 mmol) were taken in a 10 mL reaction vessel. This reaction mixture was subjected the microwave irradiation, in which the microwave power was 250 W, to attain a reaction temperature of 1 50° C. After this reaction proceeded for 30 min, water (200 mL) was added to the reaction mixture and the reaction product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate concentrated under vacuum. The product was purified through column chromatography using 230-400 mesh silica gel to afford the desired compound as light yellow solid (290 mg, yield, 35%).

Workup

  1. customwere taken in a 10 mL reaction vessel
  2. customthe microwave irradiation
  3. customa reaction temperature of 1 50° C
  4. extractionthe reaction product was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe product was purified through column chromatography

Sources & evidence

ORD record
ord-458853a9b8f0463faac5550aadee6ad7
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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