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

HRID 1746139Notes

Reaction equation

HRID 1746139 reaction equation
Br[C:2]1[CH2:6][CH2:5][O:4][N:3]=1.COC(=O)[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][N:11]=1>>[N:11]1[CH:10]=[CH:15][CH:14]=[C:13]([O:16][C:2]2[CH2:6][CH2:5][O:4][N:3]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 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-215a and I-215b were prepared in 2 steps compound from racemic compound I-21. Bromo-4,5-dihydroisoxazole I-21 was reacted with 5-hydroxy picolinic 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]+=418.3 m/z. Activity: B

Workup

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

Sources & evidence

ORD record
ord-9c8fbccc2892440e9c5ee4a48bc2d3d2
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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