Ethyl Acetate → 2-Methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-1-methyl-ethyl]-amide
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5](/[C:8](=[N:10]/[S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])/[CH3:9])=[CH:4][CH:3]=1.[CH3:17][Mg]Br.[NH4+].[Cl-].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])([CH3:17])[CH3:9])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Crude 2-methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-eth-(E)-ylidene]-amide (56 mg, 0.22 mmol) was dissolved in dry THF (2.2 mL) and cooled to −20° C. under an atmosphere of inert gas. Methylmagnesium bromide (1.0 M in MePh/THF, 0.26 mL, 0.26 mmol) was added in one portion via syringe and the reaction was stirred −20° C. for 1.5 h. To the reaction mixture was added saturated aqueous NH4Cl (4 mL) and EtOAc (7 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over Na2SO4, concentrated and then purified by flash chromatography (silica, 0→4% MeOH/CH2Cl2). 15 mg of impure 2-methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-1-methyl-ethyl]-amide was isolated as a light brown solid. This material was used without further purification.
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated
- custompurified by flash chromatography (silica, 0→4% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-1beb133377424500a9b65bec9d742398
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575360B2
Reaction notes
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