Sodium hydride → HCID 68871620, compound

HRID 1986384Notes

Reaction equation

HRID 1986384 reaction equation
Br[C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17].[H-].[Na+]>CN(C=O)C>[NH2:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([O:12][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 88068Methyl 3-HydroxybenzoateHCID 130404032-Bromo-5-nitropyridin-4-amine

Product 1

HCID 68871620HCID 68871620, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Under nitrogen, to a solution of 2-bromo-5-nitro-4-pyridineamine (3.67 g, 16.8 mmol) and methyl 3-hydroxybenzoate (2.82 g, 18.5 mmol) in DMF (100 mL), was added NaH (810 mg, 60% suspension, 20.2 mmol). 5 min later, the reaction mixture was heated to 65° C. The reaction mixture was concentrated, taken up in EtOAC, washed with NaOH solution (1.0N), saturated NH4Cl solution and brine, dried over Na2SO4, filtered and concentrated to afford the title compound, which was used directly to next step without further purification. MS (ES+) m/e 290 [+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with NaOH solution (1.0N), saturated NH4Cl solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec46cbc5431345bb9369178d5ae3115b
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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