2-Bromo-5-hydroxypyridine → 3-(Pyridin-3-yloxy)-4,5-dihydroisoxazole

HRID 1746140Notes

Reaction equation

HRID 1746140 reaction equation
FC(F)(F)C1C=CC(C=C)=CC=1.Br[C:14]1[CH2:18][CH2:17][O:16][N:15]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][N:21]=1>>[N:21]1[CH:20]=[CH:25][CH:24]=[C:23]([O:26][C:14]2[CH2:18][CH2:17][O:16][N:15]=2)[CH:22]=1

Participants

4

Reactant 3

HCID 27628652-Bromo-5-hydroxypyridineHCID 27827981-Ethenyl-4-(trifluoromethyl)benzeneHCID 219834983-Bromo-4,5-dihydroisoxazole

Product 1

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

Procedure

3-(pyridin-3-yloxy)-4,5-dihydroisoxazole I-216a and I-216b 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 2-bromo-5-hydroxypyridine using Method 5 to provide racemic compound I-216. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=389.1 m/z. Activity: B

Workup

  1. customto provide racemic compound I-216
  2. customThese compounds can be separated

Sources & evidence

ORD record
ord-c9ca2433262d4f3786b81021a64e74c2
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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