1-Ethenyl-4-(trifluoromethyl)benzene → 3-(Pyridin-3-yloxy)-4,5-dihydroisoxazole

HRID 1746146Notes

Reaction equation

HRID 1746146 reaction equation
FC(F)(F)C1C=CC(C=C)=CC=1.Br[C:14]1[CH2:18][CH2:17][O:16][N:15]=1.CS[C:21]1[N:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1>>[N:26]1[CH:21]=[CH:22][CH:23]=[C:24]([O:27][C:14]2[CH2:18][CH2:17][O:16][N:15]=2)[CH:25]=1

Participants

4

Reactant 3

HCID 27827981-Ethenyl-4-(trifluoromethyl)benzeneHCID 219834983-Bromo-4,5-dihydroisoxazoleHCID 231452196-(Methylthio)pyridin-3-OL

Product 1

HCID 668185323-(Pyridin-3-yloxy)-4,5-dihydroisoxazole

Procedure

3-(pyridin-3-yloxy)-4,5-dihydroisoxazole I-238a and I-238b were prepared in 2 steps from 1-(trifluoromethyl)-4-vinylbenzene using the cycloaddition conditions from Method 1. The resulting bromo-4,5-dihydroisoxazole was reacted with 6-(methylthio)pyridin-3-ol (prepared from 6-(methylthio)pyridin-3-ylboronic acid using Method 11) using Method 5 to provide compound I-238. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=355.3 m/z. Activity: A

Workup

  1. customto provide compound I-238
  2. customThese compounds can be separated

Sources & evidence

ORD record
ord-25ac8f753f1d4a1aa4535477f115df14
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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