2-Aminopyridine → HCID 57786669, compound

HRID 1969102Notes

Reaction equation

HRID 1969102 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:10][C:11]1[CH:12]=[C:13](Cl)[C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[N:16]=1>CN(C)C=O>[Cl:10][C:11]1[CH:12]=[C:13]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[N:16]=1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 575175396,8-Dichloroimidazo[1,2-b]pyridazine

Product 1

HCID 57786669HCID 57786669, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-aminopyridine (0.388 g, 4.12 mmol) in 8 mL of N,N-dimethylformamide was treated with 60% sodium hydride/mineral oil (0.167 g, 4.18 mmol) and the lightly bubbling, pale yellow solution was stirred for 30 min., in which time it became a dark yellow cloudy solution. The solution was added via Pasteur pipette to a flask containing 6,8-dichloro-imidazo[1,2-b]pyridazine (0.310 g, 1.65 mmol), and the cloudy orange solution was stirred for 16 h then partitioned between 80 mL of a saturated aq. NH4Cl solution and 80 mL of ether. The organic layer was sequentially washed with two 40 mL portions of water and 40 mL of a saturated aq. NaCl solution; dried over MgSO4, filtered and concentrated to a pale yellow solid. Column chromatography (0->33% EtOAc/hexanes) afforded 0.141 g (35%) of (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-pyridin-2-yl-amine as a white solid.

Workup

  1. customthe lightly bubbling
  2. additionThe solution was added via Pasteur pipette to a flask
  3. stirringthe cloudy orange solution was stirred for 16 h
  4. customthen partitioned between 80 mL of a saturated aq. NH4Cl solution and 80 mL of ether
  5. washThe organic layer was sequentially washed with two 40 mL portions of water and 40 mL of a saturated aq. NaCl solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a pale yellow solid

Sources & evidence

ORD record
ord-552038548e9a4dd5b006d0bd11a6733b
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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