Sodium hydride → HCID 86682700, compound

HRID 1755296Notes

Reaction equation

HRID 1755296 reaction equation
[CH3:1][C:2]1([CH3:7])[CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].Br[C:11]1[C:12]2[N:13]([CH:18]=[CH:19][N:20]=2)[N:14]=[C:15]([Cl:17])[CH:16]=1>CN(C=O)C>[Cl:17][C:15]1[CH:16]=[C:11]([N:3]2[CH2:4][CH2:5][CH2:6][C:2]2([CH3:7])[CH3:1])[C:12]2[N:13]([CH:18]=[CH:19][N:20]=2)[N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4147732,2-DimethylpyrrolidineHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 86682700HCID 86682700, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2-dimethylpyrrolidine (0.248 g, 2.5 mmol) in DMF (8 mL) was added NaH (0.060 g, 60% dispersion in mineral oil, 2.5 mmol) and stirred for 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.233 g, 1 mmol) under N2. The mixture was stirred at room temperature for 16 h. Then it was partitioned between 15 mL of saturated NH4Cl solution and 15 mL of ether. The organic layer was washed with water (10 mL×3) and saturated NaCl solution (10 mL×3), dried over NaSO4, concentrated in vacuo, and purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give 6-chloro-8-(2,2-dimethylpyrrolidin-1-yl)imidazo[1,2-b]pyridazine (0.140 g, 22%) as a light brown solid. LC-MS: [M+H]+, 251.1, tR=1.698 min.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. customThen it was partitioned between 15 mL of saturated NH4Cl solution and 15 mL of ether
  3. washThe organic layer was washed with water (10 mL×3) and saturated NaCl solution (10 mL×3)
  4. dry with materialdried over NaSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-525e48a000a748dc8e0cdd3746179395
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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