2-Amino-6-bromopyridine → 6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-amine

HRID 2359915Notes

Reaction equation

HRID 2359915 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]([NH2:28])[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]([NH2:28])[CH:25]=[CH:24][CH:23]=3)[CH:10]=[N:11]2)[CH:15]=1

Participants

4

Reactant 2

HCID 3008092-Amino-6-bromopyridineHCID 574162183-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine

Product 1

HCID 583368116-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-amine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
75 °C

Procedure

Under argon, 3.17 g (11.7 mmol) of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyridine, 2.02 g (11.7 mmol) of 6-bromopyridine-2-amine and 945 mg (817 μmol) of tetrakis(triphenylphosphine)palladium were added to a mixture, degassed by means of argon, of 23.3 ml of 2 M sodium carbonate solution in water and 63.3 ml of acetonitrile. The reaction mixture was heated to 75° C. for 18 hours, diluted with acetonitrile after cooling, dried over MgSO4, filtered and concentrated. The crude product thus obtained was purified by chromatography (acetonitrile/acetone).

Workup

  1. customdegassed by means of argon, of 23.3 ml of 2 M sodium carbonate solution in water and 63.3 ml of acetonitrile
  2. additiondiluted with acetonitrile
  3. temperatureafter cooling
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-befff1e4aba1430aa8402286f42e4577
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

Loading…