2-Methyl-propane-2-sulfonic acid 4-bromo-3-fluoro-benzylideneamide → HCID 86688557, compound

HRID 1617321Notes

Reaction equation

HRID 1617321 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:19]=[CH:18][C:8]([CH:9]=[N:10][S:11]([C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:7][C:6]=1[F:20]>C1COCC1>[Br:4][C:5]1[CH:19]=[CH:18][C:8]([CH:9]([NH:10][S:11]([C:14]([CH3:16])([CH3:17])[CH3:15])(=[O:13])=[O:12])[CH3:1])=[CH:7][C:6]=1[F:20]

Participants

4

Reactant 2

HCID 866885562-Methyl-propane-2-sulfonic acid 4-bromo-3-fluoro-benzylideneamideHCID 178418573HCID 178418573, compound

Product 1

HCID 86688557HCID 86688557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under inert gas atmosphere 37.2 mL (112 mmol) of a 3N solution of methyl magnesium bromide in THF are added dropwise to 17.1 g (55.8 mmol) 2-methyl-propane-2-sulfonic acid 4-bromo-3-fluoro-benzylideneamide (IX.1) in 170 mL THF at −78° C. The cooling bath is removed and stirring is continued for 2 h. After that time, the mixture is poured into sat. NH4Cl-solution (300 mL) and extracted with EtOAc. The organic layer is separated, washed with brine and dried over sodium sulphate. The solvent is removed by evaporation to yield the desired product.

Workup

  1. customThe cooling bath is removed
  2. additionAfter that time, the mixture is poured into sat. NH4Cl-solution (300 mL)
  3. extractionextracted with EtOAc
  4. customThe organic layer is separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. customThe solvent is removed by evaporation

Sources & evidence

ORD record
ord-d9acbc1ddeec43d480c06bc3b41481ff
Source dataset
uspto-grants-2014_07
Patent number
US08765959B2

Reaction notes

Loading…