2-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol → 5-[4-fluoro-3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)phenyl]-2-trifluoromethyl-[1,8]naphthyridine

HRID 1061835Notes

Reaction equation

HRID 1061835 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[N:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[OH:22].Cl.Cl[CH2:25][C:26]1[N:30]([CH3:31])[N:29]=[CH:28][N:27]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][C:14]([C:18]([F:19])([F:20])[F:21])=[N:13]3)=[CH:4][C:3]=1[O:22][CH2:25][C:26]1[N:30]([CH3:31])[N:29]=[CH:28][N:27]=1

Participants

3

Reactant 2

HCID 222853142-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenolHCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride

Product 1

HCID 101357735-[4-fluoro-3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)phenyl]-2-trifluoromethyl-[1,8]naphthyridineYield 58.6%

Procedure

2-Fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenol (50.0 mg, 0.16 mmol) was alkylated with 5-chloromethyl-1-methyl-1H-[1,2,4]triazole hydrochloride (prepared as described in WO 0023449, 30.4 mg, 0.20 mmol) as described in Example 47, affording 5-[4-fluoro-3-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)phenyl]-2-trifluoromethyl-[1,8]naphthyridine (37.8 mg, 58%). δH (360 MHz, CDCl3) 4.06 (3H, s), 5.39 (2H, s), 7.08-7.12 (1H, m), 7.28-7.36 (2H, m), 7.51 (1H, d, J 4.2), 7.82 (1H, d, J 8.8), 7.87 (1H, s), 8.43 (1H, d, J 8.4), 9.27 (1H, d, J 4.6). m/z (ES+) 404 [MH]+.

Sources & evidence

ORD record
ord-aaf1b9f6eecc463f9d1fb7f42119604a
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

Loading…