HCID 11580240, compound → HCID 11716374, compound

HRID 724732Notes

Reaction equation

HRID 724732 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[F:18])[S:6]1(=[O:20])=[O:19])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[F:18])[S:6]1(=[O:19])=[O:20])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11580240HCID 11580240, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11716374HCID 11716374, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-tert-Butyl-5-(2-fluoro-4-methylphenyl)isothiazol-3(2H)-one 1,1-dioxide (4.5 g) in ethanol (120 mL) was treated with palladium (900 mg, 8.46 mmol) (10% palladium on carbon) and placed on a par hydrogenator under a 50 psi atmosphere of hydrogen for 24 h. The reaction was filtered though celite. After concentration, the crude material was purified by silica gel chromatography (3–10% ethyl acetate:hexanes) to afford product as a white solid (3.6 g, 79%). 1H NMR (400 MHz, CDCl3): δ7.21–7.17 (m, 1H), 7.02–6.96 (m, 2H), 5.04 (dd, J=9.0, 7.0 Hz, 1H), 3.26 (dd, J=17.2, 9.0 Hz, 1H), 3.08 (dd, J=17.2, 7.0 Hz, 1H), 2.37 (s, 3H), 1.66 (s, 9H).

Workup

  1. filtrationThe reaction was filtered though celite
  2. concentrationAfter concentration
  3. customthe crude material was purified by silica gel chromatography (3–10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-ec71ad3cd5be40fea442cae3e8c1445d
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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