4-Butoxybenzaldehyde → 3-(Pyridin-3-yloxy)-4,5-dihydroisoxazole

HRID 1746126Notes

Reaction equation

HRID 1746126 reaction equation
C(OC1C=CC(C=O)=CC=1)CCC.Br[C:15]1[CH2:19][CH2:18][O:17][N:16]=1.COC(=O)[C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][N:24]=1>>[N:24]1[CH:23]=[CH:28][CH:27]=[C:26]([O:29][C:15]2[CH2:19][CH2:18][O:17][N:16]=2)[CH:25]=1

Participants

4

Reactant 3

HCID 798134-ButoxybenzaldehydeHCID 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-137a and I-137b were prepared in 3 steps from 4-butoxybenzaldehyde using Method 8 followed by cycloaddition using Method 1. The resulting bromo-4,5-dihydroisoxazole was reacted with 5-hydroxypicolinic acid methyl ester using Method 5. These compounds can be separated using chiral HPLC methods known in the art. For example, see chiral HPLC Method disclosed herein. [M+H]+=370.1 m/z. Activity: A

Workup

  1. customThese compounds can be separated

Sources & evidence

ORD record
ord-068d70c0d6b74d9082d212cf6828b542
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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