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

HRID 1746128Notes

Reaction equation

HRID 1746128 reaction equation
C(OC1C=CC(C=O)=CC=1)(C)C.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 2500774-IsopropoxybenzaldehydeHCID 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-140a and I-140b were prepared in 4 steps from 4-iso-propoxybenzaldehyde 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 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]+=343.5 m/z. Activity: A

Workup

  1. customfollowed by hydrolysis
  2. customcan be separated

Sources & evidence

ORD record
ord-e55a97af0e9c4f0980b918edead596e2
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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