Sodium Hydroxide → HCID 56773886, compound

HRID 2387292Notes

Reaction equation

HRID 2387292 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:12]Br.[OH-].[Na+]>CC(O)=O>[Br:12][C:9]1[C:8]([NH2:11])=[CH:7][CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[N:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 200389776-(Methanesulfonyl)pyridin-3-amine

Product 1

HCID 56773886HCID 56773886, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 510 mg (2.96 mmol) of 6-methanesulfonylpyridin-3-ylamine in 1.25 mL of AcOH was added a solution of 0.15 mL (2.96 mmol) of bromine in 0.5 mL of AcOH at room temperature dropwise. The resulting slurry was stirred for 1 hour. The reaction was carefully basified to pH=10 with 6 M NaOH. The solution was then extracted with two 150 mL portions of dichloromethane, dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture showed a 3:1 mixture of product:dibromo product by NMR. These two products were separated by silica chromatography (hexanes/EtOAc) to afford 294 mg (40%) of 2-bromo-6-methanesulfonylpyridin-3-ylamine.

Workup

  1. extractionThe solution was then extracted with two 150 mL portions of dichloromethane
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additiona 3:1 mixture of product
  6. customThese two products were separated by silica chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-a003a8bcf99d4cdba9a021014d50d09f
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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