Sodium hydride → HCID 18466613, compound

HRID 2229348Notes

Reaction equation

HRID 2229348 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:12]([NH:21][CH2:22][CH3:23])=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[O:9])=[CH:6][C:5]([Br:24])=[CH:4][N:3]=1.[H-].[Na+]>CN(C=O)C.O>[Br:24][C:5]1[CH:4]=[N:3][C:2]2[N:21]([CH2:22][CH3:23])[C:12]3[N:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=3[NH:10][C:8](=[O:9])[C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 18466631HCID 18466631, compound

Product 1

HCID 18466613HCID 18466613, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-N-{2-(ethylamino)-6-(trifluoromethyl)-3-pyridinyl}-5-bromo-3-pyridinecarboxamide (766 mg, 1.8 mmol) in DMF (18 mL) was added NaH (137 mg, 5.4 mmol). The reaction was stirred at 80° C. After 1 h the reaction was allowed to cool to room temperature, and then was poured in water (20 mL). The resulting mixture was extracted with EtOAc (3×). The combined organic layer was successively washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 7:3) to give the desired compound (200 mg, 28% yield) as a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe resulting mixture was extracted with EtOAc (3×)
  3. washThe combined organic layer was successively washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (hexane:EtOAc, 7:3)

Sources & evidence

ORD record
ord-b33287776ff8462ca284ad51b091f16c
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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