Sodium hydride → HCID 86682693, compound

HRID 1755285Notes

Reaction equation

HRID 1755285 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1)[CH3:2].[H-].[Na+].Br[C:13]1[C:14]2[N:15]([CH:20]=[CH:21][N:22]=2)[N:16]=[C:17]([Cl:19])[CH:18]=1.[NH4+].[Cl-]>CN(C=O)C>[Cl:19][C:17]1[CH:18]=[C:13]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=2)[C:14]2[N:15]([CH:20]=[CH:21][N:22]=2)[N:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98127775-Ethylpyridin-2-amineHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 86682693HCID 86682693, compoundYield 220.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-ethylpyridin-2-amine (394 mg, 3.23 mmol) in DMF (8 mL) was added NaH (129 mg, 60% dispersion in mineral oil, 3.23 mmol) under N2 atmosphere at room temperature and stirred for another 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[1,2-b]pyridazine (0.3 g, 1.3 mmol). After 20 h stirring at room temperature, saturated NH4Cl solution was added and the reaction mixture was extracted with ether (200 mL) and washed with water (2×50 mL), then brine (2×50 mL). After drying and filtration, it was concentrated to afford 6-chloro-N-(5-ethylpyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (785 mg, crude) as a yellow solid that was used directly without further purification. LC-MS: [M+1]+=274, tR=1.726 min.

Workup

  1. stirringAfter 20 h stirring at room temperature
  2. extractionthe reaction mixture was extracted with ether (200 mL)
  3. washwashed with water (2×50 mL)
  4. customAfter drying
  5. filtrationfiltration, it
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-7416e3b9cb8641669fc32b869e042896
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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