3-(Bromomethyl)-2-chloropyridine → 3-[4-(2-Chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid ethyl ester

HRID 929759Notes

Reaction equation

HRID 929759 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].Br[CH2:19][C:20]1[C:21]([Cl:26])=[N:22][CH:23]=[CH:24][CH:25]=1>>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:19][C:20]3[C:21]([Cl:26])=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:15][CH:16]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 189310283-(Bromomethyl)-2-chloropyridineHCID 136133842Ethyl 3-(4-hydroxyphenyl)isoxazole-5-carboxylate2×

Product 1

HCID 902025533-[4-(2-Chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid ethyl ester

Procedure

3-(4-Hydroxy-phenyl)-isoxazole-5-carboxylic acid ethyl ester (which may be prepared as described in Preparation of Intermediate 1) and 3-bromomethyl-2-chloro-pyridine (which may be prepared as described in Selby, T. P. and Winters, M. P. U.S. Pat. No. 5,739,326 Column 19) were reacted using conditions similar to those described for Preparation of Intermediate 24 to give 3-[4-(2-chloro-pyridin-3-ylmethoxy)-phenyl]-isoxazole-5-carboxylic acid ethyl ester.

Workup

  1. custom5,739,326 Column 19) were reacted

Sources & evidence

ORD record
ord-7d4d68a38fee4b21b104ed3e45d58398
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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