6-Bromopyridine-2-sulfonamide → 6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide

HRID 2359920Notes

Reaction equation

HRID 2359920 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[N:27]=[C:26]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:25]=[CH:24][CH:23]=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>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([N:12]2[CH:13]=[C:9]([C:22]3[N:27]=[C:26]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:25]=[CH:24][CH:23]=3)[CH:10]=[N:11]2)[CH:15]=1

Participants

4

Reactant 2

HCID 573458166-Bromopyridine-2-sulfonamideHCID 574162183-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine

Product 1

HCID 666336316-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide

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 (0.2 g, 0.74 mmol, prepared by the methods described in WO 2011/045224), 6-bromopyridin-2-sulphonamide (0.175 g, 0.74 mmol) and tetrakis(triphenylphosphine)palladium (0.025 g, 0.022 mmol) were added to a mixture, degassed by means of argon, of sodium carbonate solution in water (2.9 ml, 2 M/L) and acetonitrile (4 ml). The reaction mixture was stirred at 70° C. for 18 h. After cooling, the reaction mixture was poured onto water and the precipitated crystals were filtered off with suction. They were 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. additionwere added to a mixture
  2. customdegassed by means of argon, of sodium carbonate solution in water (2.9 ml, 2 M/L) and acetonitrile (4 ml)
  3. temperatureAfter cooling
  4. additionthe reaction mixture was poured onto water
  5. filtrationthe precipitated crystals were filtered off with suction
  6. stirringThey were subsequently stirred with diethyl ether
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-a29f05021e9442229f8ad18f739e5945
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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