Pyrazole → 6-(1H-pyrazol-1-yl)pyridin-3-amine

HRID 84867

Reaction equation

HRID 84867 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[NH:9]1[CH:13]=[CH:12][CH:11]=[N:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.C(Cl)(Cl)Cl>[N:9]1([C:2]2[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH:13]=[CH:12][CH:11]=[N:10]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 167748226-(1H-pyrazol-1-yl)pyridin-3-amineYield 17%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

Commercial 6-fluoropyridin-3-amine (500 mg, 4.46 mmol) was dissolved in 20 mL dry NMP. To it were added pyrazole (910 mg, 13.4 mmol) and cesium carbonate (4.4 g, 13.4 mmol). The mixture was stirred in a sealed tube at 120° C. for over the weekend (3 nights). The mixture was diluted with chloroform, washed with brine (3 times), dried, concentrated and subjected to flash column (0 to 30% EtOAc in DCM) to isolate 6-(1H-pyrazol-1-yl)pyridin-3-amine (120 mg, 17% yield).

Workup

  1. washwashed with brine (3 times)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b211c993c0db4887b1819cb46fe63efb
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Linked notes

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