Hydrogen Peroxide → HCID 178429924, compound

HRID 1625231Notes

Reaction equation

HRID 1625231 reaction equation
[OH-:1].[Na+].OO.[OH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([S:12][C:13]2[CH:20]=[C:19]([N:21]3[C:25]4=[N:26][CH:27]=[CH:28][C:29]([C:30]5[CH:31]=[N:32][C:33]6[C:38]([CH:39]=5)=[CH:37][CH:36]=[CH:35][CH:34]=6)=[C:24]4[C:23]([CH3:40])=[CH:22]3)[CH:18]=[CH:17][C:14]=2[C:15]#[N:16])[CH2:8][CH2:7]1.O>CS(C)=O.C(O)C>[OH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([S:12][C:13]2[CH:20]=[C:19]([N:21]3[C:25]4=[N:26][CH:27]=[CH:28][C:29]([C:30]5[CH:31]=[N:32][C:33]6[C:38]([CH:39]=5)=[CH:37][CH:36]=[CH:35][CH:34]=6)=[C:24]4[C:23]([CH3:40])=[CH:22]3)[CH:18]=[CH:17][C:14]=2[C:15]([NH2:16])=[O:1])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 178429918HCID 178429918, compound

Product 1

HCID 178429924HCID 178429924, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

Trans-4-mercaptocyclohexanol (0.050 g), tris(dibenzylideneacetone)dipalladium(0) (0.008 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.010 g), and N,N-diisopropylethylamine (0.116 mL) were added to a solution of (40f) (0.150 g) prepared in Example 40(6) in 1,4-dioxane (1.71 mL), followed by stirring under nitrogen flow at 120° C. for 6 hr. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and the solvent was distilled away. The residue was purified by neutral silica gel column chromatography (n-hexane/ethyl acetate) to obtain a crude product of 2-(trans-4-hydroxycyclohexylthio)-4-{3-methyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}benzonitrile. Subsequently, an aqueous sodium hydroxide solution (4 M, 0.851 mL) and a 30% hydrogen peroxide solution (0.193 mL) were added to a solution of this 2-(trans-4-hydroxycyclohexylthio)-4-{3-methyl-4-(quinolin-3-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl}benzonitrile in DMSO (0.4 mL) and ethanol (1.6 mL) at room temperature, followed by stirring for 30 min. Water was added to the reaction solution, and the precipitate was collected by filtration, washed by sprinkling water and ether, and then dried under reduced pressure to obtain (67) (0.023 g, the second stage yield: 13%) as a white solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-5c7e9c92bac143d4ba4967e681a6a253
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

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