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

HRID 1746134Notes

Reaction equation

HRID 1746134 reaction equation
FC(F)(F)C1C=CC(C=C)=CC=1.Br[C:14]1[CH2:18][CH2:17][O:16][N:15]=1.COC(=O)[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][N:23]=1>>[N:23]1[CH:22]=[CH:27][CH:26]=[C:25]([O:28][C:14]2[CH2:18][CH2:17][O:16][N:15]=2)[CH:24]=1

Participants

4

Reactant 3

HCID 27827981-Ethenyl-4-(trifluoromethyl)benzeneHCID 4715126Methyl 5-hydroxypyridine-2-carboxylateHCID 219834983-Bromo-4,5-dihydroisoxazole

Product 1

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

Procedure

3-(pyridin-3-yloxy)-4,5-dihydroisoxazole I-170a and I-170b were prepared in 3 steps from 1-(trifluoromethyl)-4-vinylbenzene using the cycloaddition conditions from Method 5. The resulting bromo-4,5-dihydroisoxazole was reacted with 5-hydroxypicolinic acid methyl ester using Method 5 followed by hydrolysis using the analogous conditions as in example 94. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=353.0 m/z. Activity: A

Workup

  1. customfollowed by hydrolysis
  2. customThese compounds can be separated

Sources & evidence

ORD record
ord-dcbadf74fadc4509990baccea2553d7d
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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