HCID 12018255, compound → HCID 18383974, compound

HRID 2297690Notes

Reaction equation

HRID 2297690 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[N:7]([CH3:20])[CH:6]=1)=[O:4].B1([O-])O[O:22]1.O.O.O.O.[Na+]>CC(O)=O>[Cl:1][CH2:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:18])=[O:22])=[CH:13][CH:12]=2)[N:7]([CH3:20])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 12018255HCID 12018255, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 18383974HCID 18383974, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.5 g (0.008 mole) of 2-chloro-1-[1-methyl-5-(4-(methylthio)benzoyl]-1H-pyrrol-3-yl]-ethanone, 1.2 g of sodium perborate tetrahydrate and 50 mL of HOAc was stirred for 3 h. The solvent was evaporated in vacuo and the residue partitioned between CH2Cl2 and NaHCO3. The organics were separated off and washed again with NaHCO3, water, brine and dried (Na2SO4). The solvent was evaporated in vacuo. The residue was passed through a Biotage flash 40 L column (silica gel 9:1 CH2Cl2: MeOH) to give 2.2 g (85%) of 2-chloro-1-[1-methyl-5-(4-(methylsulfinyl)benzoyl]-1H-pyrrol-3-yl]-ethanone. CIMS m/z=324 (MH+). HNMR (CDCl3) δ8.0 (d, 2H); 7.75 (d, 2H); 7.6 (s, 1H); 7.15 (s, 1H); 4.4 (s, 2H); 4.1 (2, 3H); 2.8 (s, 3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between CH2Cl2 and NaHCO3
  3. customThe organics were separated off
  4. washwashed again with NaHCO3, water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-60bec643dfa34cadb768c2d679012b55
Source dataset
uspto-grants-2002_12
Patent number
US06492387B2

Reaction notes

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