2-Amino-6-bromopyridine → HCID 68840742, compound

HRID 1454810Notes

Reaction equation

HRID 1454810 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH2:9]([S-:11])[CH3:10].[Na+]>CN(C=O)C>[CH2:9]([S:11][C:4]1[N:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1)[CH3:10]

Participants

4

Reactant 2

HCID 3008092-Amino-6-bromopyridineHCID 4459711Sodium ethanethiolate

Product 1

HCID 68840742HCID 68840742, compoundYield 204%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-6-bromopyridine (0.88 g) and sodium ethanethiolate (0.46 g) were dissolved in DMF (10 mL) stirred at RT for 20 h and subsequently at 60° C. for further 20 h to complete the reaction according to HPLC analysis. The mixture was concentrated in vacuo, partitioned between AcOEt and water, the layers were separated and the organic layer dried over Na2SO4, filtered and evaporated to give to give 6-ethylsulfanyl-pyridin-2-ylamine as brown oil (1.6 g) that was used directly in the next reaction step.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between AcOEt and water
  3. customthe layers were separated
  4. dry with materialthe organic layer dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give

Sources & evidence

ORD record
ord-ec23747f89aa4594917a733413382b8a
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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