HCID 88539500, compound → HCID 16102886, compound

HRID 1404565Notes

Reaction equation

HRID 1404565 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[C:4]([F:16])[CH:3]=1.[CH3:17][Mg]Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:9][S@:10]([C:12]([CH3:13])([CH3:15])[CH3:14])=[O:11])[CH3:17])=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 88539500HCID 88539500, compoundHCID 178418332HCID 178418332, compound2×

Product 1

HCID 16102886HCID 16102886, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-48 °C

Procedure

To a solution of (S)-2-methyl-propane-2-sulfinic acid 1-(4-bromo-2-fluoro-phenyl)-meth-(E)-ylideneamide (4.5 g, 14.7 mmol) in DCM (80 ml) was added methylmagnesium chloride (7.35 ml, 22.0 mmol, 3M solution in ether) dropwise at −48° C. After 1 h additional methylmagnesium chloride (2.45 ml, 7.35 mmol, 3M solution in ether) was added dropwise and the reaction mixture was stirred at −48° C. for 6 h. The reaction was then quenched by addition of sat. NH4Cl solution and the mixture was extracted three times with DCM. The combined organic layers were dried with Na2SO4 and evaporated. The remaining white solid was purified by chromatography (silica gel; heptane/EtOAc 2:1-1:1) to obtain the title compound as white solid (3.89 g, 82%).

Workup

  1. customThe reaction was then quenched by addition of sat. NH4Cl solution
  2. extractionthe mixture was extracted three times with DCM
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. customevaporated
  5. customThe remaining white solid was purified by chromatography (silica gel; heptane/EtOAc 2:1-1:1)

Sources & evidence

ORD record
ord-024abc198e904f38b00e0c9ba9dd0ec0
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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