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

HRID 2188887Notes

Reaction equation

HRID 2188887 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

HCID 59166177tert-butyl 6-(4-(N-methylsulfamoyl)phenyl)pyridin-2-ylcarbamateYield 72.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5796fe9f248041108b2ed04a39e98a2e
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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