3-Pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester → 6-(3-Pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acid

HRID 83454

Reaction equation

HRID 83454 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:14][O:15][CH:16]=2)=[N:6][CH:5]=1.C(OC(C1C(C2C=CC=CN=2)=NOC=1)=O)C>>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:23])=[O:2])=[CH:5][N:6]=2)=[CH:16][O:15][N:14]=1

Participants

3

Reactant 2

HCID 666437583-Pyridin-2-yl-isoxazole-4-carboxylic acid ethyl esterHCID 684443546-(3-Pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 684452576-(3-Pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acidYield 96.3%

Procedure

As described for example 358b, 6-(3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (510 mg, 1.6 mmol), instead of 3-pyridin-2-yl-isoxazole-4-carboxylic acid ethyl ester, was converted to the title compound (458 mg, 94%) which was obtained as a white solid. MS: m/e=296.5 [M−H]−.

Sources & evidence

ORD record
ord-53e7dcb839ed45cc954071bc24ac5194
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Linked notes

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