Potassium Carbonate → {5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfonyl)phenyl]methanol

HRID 70715Notes

Reaction equation

HRID 70715 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:20]([C:22]3[CH:27]=[CH:26][C:25](SC4CC4)=[CH:24][CH:23]=3)[OH:21])=[N:8][C:9]=2[O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.ClC1C=CC=[C:35]([C:39](OO)=O)[CH:34]=1.[S:43]([O-:47])([O-])(=[O:45])=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:20]([C:22]3[CH:23]=[CH:24][C:25]([S:43]([CH:39]4[CH2:35][CH2:34]4)(=[O:47])=[O:45])=[CH:26][CH:27]=3)[OH:21])=[N:8][C:9]=2[O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 67400247{5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol

Product 1

HCID 67400026{5-Cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfonyl)phenyl]methanolYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of {5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfanyl)phenyl]methanol (469 mg) in chloroform (15 mL) was stirred in an ice bath, and m-chloroperbenzoic acid (560 mg) was added as powder. The mixture was returned to room temperature and stirred for 3.5 hours. The reaction solution was stirred again in an ice bath, and sodium thiosulfate and a potassium carbonate solution were added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66) to give {5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridin-2-yl}[4-(cyclopropylsulfonyl)phenyl]methanol as a light yellow oil (403 mg, 80%).

Workup

  1. customwas returned to room temperature
  2. stirringThe reaction solution was stirred again in an ice bath
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66)

Sources & evidence

ORD record
ord-7f8a86eb06914d1ca74bff38a97a5f3b
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…