m-Chloroperbenzoic acid → 3-Methanesulfinyl-5-phenylethynylpyridine

HRID 606904Notes

Reaction equation

HRID 606904 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[CH3:12][S:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1>ClCCl>[CH3:12][S:13]([C:14]1[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1)=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 670478293-Methylsulfanyl-5-phenylethynylpyridine

Product 1

HCID 670476143-Methanesulfinyl-5-phenylethynylpyridineYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 3-chlorobenzenecarboperoxoic acid (27.61 mg, 0.16 mmol) to a cooled solution of 3-methylsulfanyl-5-phenylethynyl-pyridine, (prepared as described in EXAMPLE 128), (35.3 mg, 0.16 mmol) in dichloromethane (1 mL) at room temperature. Stir for 2 h and then quench with a 5% aqueous solution of sodium thiosulfite. Dilute with dichloromethane and separate the layers. Sequentially extract the organic layer with a 5% aqueous solution of sodium thiosulfite and an aqueous saturated solution of sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting from 100:0 to 100:50 with hexanes:ethyl acetate, to give the title compound (10.3 mg, 27%).

Workup

  1. customquench with a 5% aqueous solution of sodium thiosulfite
  2. additionDilute with dichloromethane
  3. customseparate the layers
  4. extractionSequentially extract the organic layer with a 5% aqueous solution of sodium thiosulfite
  5. dry with materialan aqueous saturated solution of sodium chloride, dry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue by silica gel chromatography
  9. washeluting from 100:0 to 100:50 with hexanes

Sources & evidence

ORD record
ord-314e9aa694224da2bc9a2baa16f1a25c
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

Loading…