Water → HCID 67389786, compound

HRID 906834Notes

Reaction equation

HRID 906834 reaction equation
Br[C:2]1[C:7]([NH2:8])=[C:6]([Br:9])[CH:5]=[C:4]([CH2:10][CH3:11])[N:3]=1.[S-:12][CH2:13][CH3:14].[Na+].O>CN(C=O)C>[Br:9][C:6]1[CH:5]=[C:4]([CH2:10][CH3:11])[N:3]=[C:2]([S:12][CH2:13][CH3:14])[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 962WaterHCID 4459711Sodium ethanethiolateHCID 860425942,4-Dibromo-6-ethyl-3-pyridinamine

Product 1

HCID 67389786HCID 67389786, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2,4-Dibromo-6-ethyl-pyridin-3-ylamine (105 mg, 0.38 mmoles) was combined with 80% sodium thioethoxide (50 mg, 0.48 mmoles) in anhydrous DMF (2 mL) and was stirred at 50° C. under nitrogen for 2 hours. After this period the reaction mix was combined with water (20 mL) and was extracted with EtOAc (3×20 mL). The combined EtOAc layer was washed with water (3×15 mL) and brine. After drying over anhydrous Na2SO4 the organic layer was evaporated in vacuo to yield crude product. The crude product was purified using flash silica chromatography (0-15% EtOAc/Hexane) to yield 4-bromo-6-ethyl-2-ethylsulfanyl-pyridin-3-ylamine (83 mg, 84%) as a clear residue. 1H-NMR (CDCl3): δ 6.94 (s, 1H), 4.34 (br s, 2H), 2.95 (q, J=7.3 Hz, 2H), 2.68 (q, J=7.6 Hz, 2H), 1.33 (t, J=7.3 Hz, 3H), 1.24 (t, J=7.6 Hz, 3H).

Workup

  1. additionAfter this period the reaction mix
  2. extractionwas extracted with EtOAc (3×20 mL)
  3. washThe combined EtOAc layer was washed with water (3×15 mL) and brine
  4. dry with materialAfter drying over anhydrous Na2SO4 the organic layer
  5. customwas evaporated in vacuo
  6. customto yield crude product
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-f82aac1125c74b1a9982cfa4a40c021d
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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