m-Chloroperbenzoic acid → HCID 86620845, compound

HRID 1947045Notes

Reaction equation

HRID 1947045 reaction equation
[CH:1]1C=C(Cl)C=[C:3]([C:8](OO)=O)[CH:2]=1.C(S[C:17]1[N:22]=[C:21]([N:23]2[C:31]3[C:26](=[C:27]([O:32][CH2:33][CH2:34][CH2:35][S:36]([NH2:39])(=[O:38])=[O:37])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)[CH:20]=[CH:19][N:18]=1)CCC.[S:40](=O)(O)[O-:41].[Na+]>C(Cl)Cl>[CH2:1]([C:17]1[N:18]=[CH:19][C:20](=[S:40]=[O:41])[CH:21]([N:23]2[C:31]3[C:26](=[C:27]([O:32][CH2:33][CH2:34][CH2:35][S:36]([NH2:39])(=[O:37])=[O:38])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)[N:22]=1)[CH2:2][CH2:3][CH3:8]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 69311869HCID 69311869, compound

Product 1

HCID 86620845HCID 86620845, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MCPBA (77%) was added dropwise to 3-[1-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-propane-1-sulfonic acid amide (1.317 g, 3.13 mmol) in DCM (20 mL) at 0° C. The reaction mixture was allowed to warm to RT, and stirred for 1 h. Sodium bisulfite (10%) was them added, the mixture extracted with DCM, washed with NaHCO3 solution, water, and brine, dried over sodium sulfate, filtered and the solvent removed in vacuo to yield 3-[1-(2-butyl-sulfinyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-propane-1-sulfonic acid amide (77.5%).

Workup

  1. additionadded
  2. extractionthe mixture extracted with DCM
  3. washwashed with NaHCO3 solution, water, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f249d57dc6e14496b06a43dba3518556
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

Loading…