Water → HCID 21099457, compound

HRID 1351622Notes

Reaction equation

HRID 1351622 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[CH:4][N:3]=1.[OH:16]OS([O-])=O.[K+].C(=O)(O)[O-].[Na+].[OH2:27]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])(=[O:16])=[O:27])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21099458HCID 21099458, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21099457HCID 21099457, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step 1 (2.0 g, 8.3 mmol) and OXONE® (7.7 g, 12.5 mmol) were stirred in methanol (50 mL) at room temperature for 6 days. Saturated sodium bicarbonate was added and the suspension stirred for 15 minutes before diluting with water and extracting into ethyl acetate (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo while loading onto silica. Dry flash column chromatography using 10–30% ethyl acetate/isohexane gave 2-chloro-5-[(2-fluorophenyl)sulfonyl]pyridine as a white solid (1.95 g, 86%). δH (500 MHz, d6 DMSO): 7.45–7.56 (2H, m), 7.81–7.88 (2H, m), 8.10 (1H, td, J=1.6, 7.6 Hz), 8.37–8.41 (1H, m), 8.98 (1H, d, J=2.6 Hz); m/z (ES+) 272, 274 [MH+].

Workup

  1. extractionextracting into ethyl acetate (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customDry flash column chromatography

Sources & evidence

ORD record
ord-1cadd11f6c2e40868aabdc252dbef424
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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