Water → 5-Bromo-2-methanesulfinylmethyl-pyridine

HRID 1484412Notes

Reaction equation

HRID 1484412 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][S:9][CH3:10])=[N:6][CH:7]=1.O.I([O-])(=O)(=O)=[O:13].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][S:9]([CH3:10])=[O:13])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 1156223545-Bromo-2-methylsulfanylmethyl-pyridine

Product 1

HCID 1176553745-Bromo-2-methanesulfinylmethyl-pyridineYield 76.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the stirred solution of 5-Bromo-2-methylsulfanylmethyl-pyridine (1.1 gm, 5.04 mmol) in MeOH: water (10:2 mL) at 0° C. is added sodium periodate (1.08 gm, 5.046 mmol) resulting reaction mixture is stirred RT for 5 h. After completion, solvent is evaporated under reduced pressure then residue is diluted with water and extract with EtOAc (3×50 mL). The combine organic layer is dried over sodium sulphate and evaporated under reduced pressure to get crude which is purified by combi flash using 8% MeOH:DCM as eluent to afford title compound (900 mg) as off white solid. 1NMR (400 MHz, DMSO) δ: 2.56 (s, 3H), 4.11 (d, J=12.6 Hz, 1H), 4.26 (d, J=12.64 Hz, 1H), 7.36 (d, J=8.28 Hz, 1H), 8.05-8.08 (dd, J1=2.44 Hz, J2=8.28 Hz, 1H), 8.71 (d, J=2.32 Hz, 1H). LC-MS (m/z): M+H=235.9.

Workup

  1. customresulting
  2. customreaction mixture
  3. customAfter completion, solvent is evaporated under reduced pressure
  4. additionresidue is diluted with water
  5. extractionextract with EtOAc (3×50 mL)
  6. dry with materialThe combine organic layer is dried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customto get crude which
  9. customis purified by combi flash

Sources & evidence

ORD record
ord-fb1c50079b444904a277b7dcbe8c1cf7
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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