Trifluoroacetic acid → 3-Cyclopropyl-6-[[4-(cyclopropylsulfonyl)phenyl](2,4-di fluorophenoxy)methyl]pyridin-2(1H)-one

HRID 70717Notes

Reaction equation

HRID 70717 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([C:11]2[C:12]([O:39]CC3C=CC(OC)=CC=3)=[N:13][C:14]([CH:17]([C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH:36]4[CH2:38][CH2:37]4)(=[O:35])=[O:34])=[CH:29][CH:28]=3)[O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:16]=2)[CH2:10][CH2:9]1>C(Cl)(Cl)Cl>[CH:8]1([C:11]2[C:12](=[O:39])[NH:13][C:14]([CH:17]([C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH:36]4[CH2:38][CH2:37]4)(=[O:35])=[O:34])=[CH:31][CH:32]=3)[O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673995783-Cyclopropyl-6-{[4-(cyclopropylsulfonyl)phenyl](2,4-difluorophenoxy)methyl}-2-[(4-methoxybenzyl)oxy]pyridine

Product 1

HCID 584523163-Cyclopropyl-6-[[4-(cyclopropylsulfonyl)phenyl](2,4-di fluorophenoxy)methyl]pyridin-2(1H)-oneYield 74.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (50 mg) was added to a solution of 3-cyclopropyl-6-{[4-(cyclopropylsulfonyl)phenyl](2,4-difluorophenoxy)methyl}-2-[(4-methoxybenzyl)oxy]pyridine (90 mg) in chloroform (5 mL), and the mixture was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=88:12→0:100) to give the title compound as a yellow powder (53 mg, 74%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=88:12→0:100)

Sources & evidence

ORD record
ord-f6090705c34d44e294452ccad8fe1e87
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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