6-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester → 6-((1-(2-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinic acid

HRID 402440Notes

Reaction equation

HRID 402440 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][N:16]=2)=[C:11]([CH3:25])[N:10]=[N:9]1.COC(=O)C1C=CC(OCC2N(C3C=CC(F)=CC=3)N=NC=2C)=NC=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=2)=[C:11]([CH3:25])[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 573354046-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl esterHCID 57335556methyl 6-((1-(2-fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinate

Product 1

HCID 674984666-((1-(2-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinic acidYield 86%

Procedure

As described for example 61a, methyl 6-((1-(2-fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinate (160 mg, 0.47 mmol), instead of 6-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester, was converted to the title compound (132 mg, 86%) which was obtained as a white solid. MS: m/e=327.2 [M−H]−.

Sources & evidence

ORD record
ord-34d10bf2216149f7a7c55815f8723835
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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