Sodium Thiosulfate → 2-Chloro-3-(1-fluorocyclobutyl)-6-methylpyridine 1-oxide

HRID 624993Notes

Reaction equation

HRID 624993 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[C:18]([C:19]2([F:23])[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:16]=[C:15]([CH3:24])[N:14]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[Cl:12][C:13]1[C:18]([C:19]2([F:23])[CH2:22][CH2:21][CH2:20]2)=[CH:17][CH:16]=[C:15]([CH3:24])[N+:14]=1[O-:6]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 902024992-Chloro-3-(1-fluorocyclobutyl)-6-methylpyridine

Product 1

HCID 902025652-Chloro-3-(1-fluorocyclobutyl)-6-methylpyridine 1-oxideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzoperoxoic acid (173 mg, 1.00 mmol) was added in 2 portions to a solution of 2-chloro-3-(1-fluorocyclobutyl)-6-methylpyridine (Example 130 b, 100 mg, 501 μmol) in dichloromethane (2 mL). The reaction mixture was stirred at ambient temperature for 72 h, poured onto a 10% aqueous Na2S2O3 solution (30 mL) and extracted with dichloromethane (2×40 mL). The combined organic layers were washed with ice water/brine (30 mL), dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with sat. NaHCO3 solution (30 mL) and ice water (30 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (81 mg, 74%) as yellow oil, MS (ESI): m/e=216.3 [MH+].

Workup

  1. extractionextracted with dichloromethane (2×40 mL)
  2. washThe combined organic layers were washed with ice water/brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with sat. NaHCO3 solution (30 mL) and ice water (30 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e6f35e3eddb4e7cb0b3b8c060ba9254
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

Loading…