HCID 18986082, compound → HCID 70818550, compound

HRID 331519Notes

Reaction equation

HRID 331519 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]Br)[CH:3]=1.[CH3:10][S:11][Na]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:11][CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 18986082HCID 18986082, compoundHCID 178504583HCID 178504583, compound

Product 1

HCID 70818550HCID 70818550, compoundYield 12.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude 4-bromo-2-(bromomethyl)pyridine was dissolved in N,N-dimethylformamide (3.000 mL), and mixture was cooled on an ice bath followed by the portion wise addition of methylsulfanylsodium (2.037 g, 29.07 mmol). Reaction mixture was left to stir for 10 minutes. The mixture was diluted with ethyl acetate, organic layer was washed with water and brine. Organic layer was extracted, dried over MgSO4 and concentrated in vacuo to a solid. Residue was purification by silica gel column chromatography loaded with dichloromethane and eluted with 50% diethylether/petroleum ether. Product fractions were combined and concentrated in vacuo to give the sub-titled product (0.8 g, 12.6%). 1H NMR (400.0 MHz, DMSO-d6) δ 2.25 (s, 3H), 3.80 (s, 2H), 7.4 (d, 1H), 7.6 (s, 1H), 8.4 (d, 1H); LC/MS m/z 220.1 [M+H]+.

Workup

  1. temperaturemixture was cooled on an ice bath
  2. customReaction mixture
  3. waitwas left
  4. washwas washed with water and brine
  5. extractionOrganic layer was extracted
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo to a solid
  8. custompurification by silica gel column chromatography
  9. washeluted with 50% diethylether/petroleum ether
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-699a6384a9e04e1da1ea0d9eaed5f5aa
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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