Lawesson's reagent → HCID 86662095, compound

HRID 2067102Notes

Reaction equation

HRID 2067102 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=O)[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:10]2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1.O1CCOCC1>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[S:34])[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 86662096HCID 86662096, compound

Product 1

HCID 86662095HCID 86662095, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 1-[(6-bromopyridin-3-yl)methyl]-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate [(Example 1, Step 6) 580 mg, 1.49 mmol] was suspended in toluene (5 mL) and dioxane (5 mL), placed into an oil bath preheated to 110° C. and treated in one portion with Lawesson's Reagent (603 mg, 1.49 mmol, 1 equiv). After stirring for 30 minutes, the mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 50:50; hexanes:ethyl acetate), providing the titled compound.

Workup

  1. custompreheated to 110° C.
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel gradient chromatography (100:0 to 50:50; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-51200981371e4ab697cf6e63782650a3
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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