HCID 11476994, compound → HCID 11397262, compound

HRID 1796336Notes

Reaction equation

HRID 1796336 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[OH:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.CCOC(C)=O>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=2[CH3:15])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:28])=[CH:23][CH:22]=2)(=[O:19])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 11476994HCID 11476994, compound

Product 1

HCID 11397262HCID 11397262, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

{4-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenyl}-phenyl-methanol, prepared as described in Example 53, (60 mg, 0.127 mmol) was dissolved in CHCl3 (2 mL) and Des-Martin periodinane (59 mg, 0.140 mmol) was added. The reaction was stirred at 25° C. for 1.5 h, dissolved in EtOAc (100 mL), and the EtOAc was washed with sat. sodium thiosulfate solution (20 mL), water (20 mL) and brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes eluent to give {4-[6-methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenyl}-phenyl-methanone (59 mg, 99% yield) as a solid, mp 222–225° C. mass spec. (AP+): m/z 471 (M+1).

Workup

  1. additionDes-Martin periodinane (59 mg, 0.140 mmol) was added
  2. washthe EtOAc was washed with sat. sodium thiosulfate solution (20 mL), water (20 mL) and brine
  3. customdried
  4. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes eluent

Sources & evidence

ORD record
ord-e353d1026f54421598f86e192a5662aa
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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