3-(2,5-Difluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester → 6-[3-(2,5-Difluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-N-isopropyl-nicotinamide

HRID 83378Notes

Reaction equation

HRID 83378 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])=[N:8][O:9][C:10]=1[CH3:11])=O)[CH3:2].C(O[C:23]([C:25]1[C:26](C2C=CC=CC=2F)=[N:27][O:28][C:29]=1C)=O)C>>[F:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[C:7]1[C:6]([CH2:4][O:3][C:1]2[CH:2]=[CH:23][C:25]([C:29]([NH:8][CH:7]([CH3:12])[CH3:6])=[O:28])=[CH:26][N:27]=2)=[C:10]([CH3:11])[O:9][N:8]=1

Participants

3

Reactant 2

HCID 684420783-(2,5-Difluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl esterHCID 68442729Ethyl 3-(2-fluorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 426301646-[3-(2,5-Difluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-N-isopropyl-nicotinamideYield 21%

Procedure

As described for example 84d, 3-(2,5-difluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (18 g, 67.4 mmol) was converted, instead of 3-(2-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester, to the title compound (3.25 g, 21%) which was obtained as a yellow oil. MS: m/e=226.2 [M+H]+.

Sources & evidence

ORD record
ord-227a64907b5d49e48600d0fb3b248877
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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