6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid methyl ester → 6-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid

HRID 402388Notes

Reaction equation

HRID 402388 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[N:13]([CH3:24])[N:14]=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=2)=[N:6][CH:5]=1.COC(=O)C1C=CC(OCC2N(C)N=NC=2C2C=CC=CN=2)=NC=1>>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]2[N:15]=[N:14][N:13]([CH3:24])[C:12]=2[CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[CH:5][N:6]=2)=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 573346466-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid methyl esterHCID 573347936-[5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 674988746-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acidYield 102.5%

Procedure

As described for example 26a, 6-[5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester (396 mg, 0.8 mmol), instead of 6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-nicotinic acid methyl ester, was converted to the title compound (270 mg, 81%) which was obtained as a white solid. MS: m/e=328.3 [M−H]−.

Sources & evidence

ORD record
ord-1aa730e819aa475e8f44b566a8f61d5d
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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