Methyl 6-chloro-4-(trifluoromethyl)nicotinate → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-4-trifluoromethyl-nicotinic acid methyl ester

HRID 83169Notes

Reaction equation

HRID 83169 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].Cl[C:16]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:17]=1>>[CH3:23][O:22][C:20](=[O:21])[C:19]1[C:24]([C:26]([F:27])([F:28])[F:29])=[CH:25][C:16]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 684449336-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-4-trifluoromethyl-nicotinic acid methyl ester

Procedure

As described for example 5, (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (3.47 g, 18.4 mmol) was converted using methyl 6-chloro-4-(trifluoromethyl)nicotinate instead of 6-chloronicotinonitrile to the title compound which was used directly in the next transformation without further purification.

Sources & evidence

ORD record
ord-8624ef20a24f46cdaa2769cf4f91f113
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

Loading…