Potassium Carbonate → tert-butyl 6-(4-(N-methylsulfamoyl)phenyl)pyridin-2-ylcarbamate

HRID 881129

Reaktionsgleichung

Reaktionsgleichung von HRID 881129
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[C:15]([O:19][C:20](=[O:29])[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](Br)[N:23]=1)([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:24]2[N:23]=[C:22]([NH:21][C:20](=[O:29])[O:19][C:15]([CH3:17])([CH3:16])[CH3:18])[CH:27]=[CH:26][CH:25]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 13040380Tert-butyl (6-bromopyridin-2-YL)carbamateHCID 441187634-((Methylamino)sulphonyl)benzene boronic acid

Produkt 1

HCID 59166177tert-butyl 6-(4-(N-methylsulfamoyl)phenyl)pyridin-2-ylcarbamateAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-(N-methylsulfamoyl)phenylboronic acid (17.2 g, 0.08 mol) and (6-bromo-pyridin-2-yl)carbamic acid tert-butyl ester (21.9 g, 0.08 mol) in DMF (125 mL) and H2O (125 mL) were added Pd(PPh3)4 (9.2 g, 0.008 mol) and K2CO3 (16.6 g, 0.12 mol). The resulting mixture was degassed by gently bubbling argon through the solution for 5 minutes at 20° C. The reaction mixture was then heated at 80° C. for 16 h. The mixture was evaporated under reduced pressure, then poured into H2O, and extracted with EtOAc. The organic phase was dried over Na2SO4, and was evaporated under reduced pressure to give tert-butyl 6-(4-(N-methylsulfamoyl)phenyl)pyridin-2-ylcarbamate (21 g, 58%), which was used in the next step without further purification.

Aufarbeitung

  1. customThe resulting mixture was degassed by gently bubbling argon through the solution for 5 minutes at 20° C
  2. customThe mixture was evaporated under reduced pressure
  3. additionpoured into H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customwas evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ce353bf459394d0491bb9dfe0f139411
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993600B2

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