Sodium hydride → (4-Bromo-2-methyl-2H-pyrazol-3-yl)-(6-phenyl-pyridin-2-yl)-amine

HRID 919083Notes

Reaction equation

HRID 919083 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[NH2:8].Cl[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[NH:8][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6003514-Bromo-1-methyl-1H-pyrazol-5-amineHCID 27628802-Chloro-6-phenylpyridine

Product 1

HCID 67957971(4-Bromo-2-methyl-2H-pyrazol-3-yl)-(6-phenyl-pyridin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-2-methyl-2H-pyrazol-3-ylamine (0.2 g, 1.14 mmol) and 2-chloro-6-phenyl-pyridine (0.32 g, 1.7 mmol) were dissolved in DMF (5 mL) then sodium hydride (60% dispersion in oil, 0.09 g, 2.3 mmol) was added. The reaction was heated to 100° C. for 30 minutes then cooled and submitted to standard aqueous workup. The residue was purified on silica gel (0-40% EtOAc in hexanes) to provide the title compound.

Workup

  1. temperaturethen cooled
  2. customThe residue was purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-340d5ce61ccc4681a4beb6c20494da88
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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