p-Toluenesulfonic acid → HCID 86682703, compound

HRID 1755300Notes

Reaction equation

HRID 1755300 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[Br:18].Cl[CH2:20][CH:21](OCC)OCC.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[Br:18][C:3]1[C:2]2[N:7]([CH:20]=[CH:21][N:1]=2)[N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 121282-Chloro-1,1-diethoxyethaneHCID 86682702Methyl 3-(6-amino-5-bromopyridazin-3-yl)benzoate

Product 1

HCID 86682703HCID 86682703, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of methyl 3-(6-amino-5-bromopyridazin-3-yl)benzoate (1 g, 3.25 mmol), 2-chloro-1,1-diethoxyethane (0.6 g, 3.9 mmol), PTSA (0.62 g, 3.9 mmol) in isopropanol (10 mL) was heated to 80° C. for 40 h. After cooling to room temperature, the solution was concentrated in vacuo. The resulting mixture was treated with a saturated NaHCO3 solution (50 mL), extracted with dichloromethane (50 mL×3), dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give methyl 3-(8-bromoimidazo[1,2-b]pyridazin-6-yl)benzoate (0.6 g, 56%) as a white solid. LC-MS: [M+H]+, 332.0, 333.9, tR=1.520 min.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionThe resulting mixture was treated with a saturated NaHCO3 solution (50 mL)
  3. extractionextracted with dichloromethane (50 mL×3)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c5150a5e1bb1482b83142912f464bf5c
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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