3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine → HCID 66633797, compound

HRID 2359923Notes

Reaction equation

HRID 2359923 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:13]=2)O1.Br[C:22]1[S:23][CH:24]=[C:25]([C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:28])[N:26]=1>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>[CH3:33][S:30]([NH:29][C:27]([C:25]1[N:26]=[C:22]([C:9]2[CH:10]=[N:11][N:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:13]=2)[S:23][CH:24]=1)=[O:28])(=[O:31])=[O:32]

Participants

4

Reactant 2

HCID 574162183-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridineHCID 66633262HCID 66633262, compound

Product 1

HCID 66633797HCID 66633797, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

Under argon, 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyridine (0.1 g, 0.37 mmol), 2-bromo-N-(methylsulphonyl)-1,3-thiazole-4-carboxamide (0.105 g, 0.37 mmol) and tetrakis(triphenylphosphine)palladium (0.013 g, 0.011 mmol) were added to a mixture, degassed by means of argon, of sodium carbonate solution in water (1.5 ml, 2 M/L) and acetonitrile (3.8 ml). The reaction mixture was stirred at 70° C. for 16 h. After cooling, the reaction mixture was poured onto water and extracted with dichloromethane. The organic phase was dried over sodium sulphate and the solvent was removed under reduced pressure. The residue was subsequently stirred with diethyl ether and filtered off with suction. This gave 0.23 g (97% of theory) of 6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide.

Workup

  1. customdegassed by means of argon, of sodium carbonate solution in water (1.5 ml, 2 M/L) and acetonitrile (3.8 ml)
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. customthe solvent was removed under reduced pressure
  7. stirringThe residue was subsequently stirred with diethyl ether
  8. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-3b9ffcbbdc784a1c8b65f52c1baeadc4
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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