Sodium hydride → HCID 21865557, compound

HRID 857305Notes

Reaction equation

HRID 857305 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:9].[H-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17]>C1COCC1.O>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:9])=[O:17]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74377Benzoyl chloride, 3-bromo-HCID 898884-Amino-3,5-dichloropyridine

Product 1

HCID 21865557HCID 21865557, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-amino 3,5-dichloro pyridine in THF (0.5M) at 0° C. was added NaH (1.5 eq). The mixture was stirred at 0° C. for 30 min then 3-bromo benzoyl chloride (2.0 eq.) was added dropwise. The resulting mixture was stirred 12 hours at room temperature, poured in water and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2 SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 1:1) afforded the desired compound a yellow solid.

Workup

  1. stirringThe resulting mixture was stirred 12 hours at room temperature
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. customdried over Na2 SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-42d395af7c3c45668c3db740a2901416
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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