Sodium hydride → HCID 117874477, compound

HRID 715929Notes

Reaction equation

HRID 715929 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[H-].[Na+].[Br:12][C:13]1[N:17]2[N:18]=[C:19](Cl)[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:12][C:13]1[N:17]2[N:18]=[C:19]([O:6][CH2:5][C:4]3[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=3)[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 680083-Fluorobenzylic alcoholHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 117874477HCID 117874477, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluorobenzyl alcohol (0.59 g) in N,N-dimethylformamide (20 ml), sodium hydride (55% oil, 0.26 g) was added under ice cooling, and the mixture was stirred at the same temperature as above for 10 minutes. 3-Bromo-6-chloroimidazo[1,2-b]pyridazine (1 g) was added to the reaction solution, and the mixture was stirred at the same temperature as above for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with water and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was washed with n-hexane to obtain the title compound (1.2 g).

Workup

  1. stirringthe mixture was stirred at the same temperature as above for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with water and saturated saline in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washThe obtained residue was washed with n-hexane

Sources & evidence

ORD record
ord-bec3f0a488d34840b103221ac0731188
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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