4-(5-bromo-2-fluorophenoxymethyl)-1-methyl-1H-[1,2,3]triazole → Imidazo[1,2-a]pyridine,8-fluoro-3-[4-fluoro-3-[(1-methyl-1h-1,2,3-triazol-4-yl)methoxy]phenyl]-7-(trifluoromethyl)-

HRID 1180323Notes

Reaction equation

HRID 1180323 reaction equation
[F:1][C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].Br[C:16]1[CH:17]=[CH:18][C:19]([F:30])=[C:20]([CH:29]=1)[O:21][CH2:22][C:23]1[N:24]=[N:25][N:26]([CH3:28])[CH:27]=1>>[F:1][C:2]1[C:3]2[N:4]([C:12]([C:16]3[CH:17]=[CH:18][C:19]([F:30])=[C:20]([O:21][CH2:22][C:23]4[N:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:29]=3)=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

3

Reactant 2

HCID 179648304-(5-bromo-2-fluorophenoxymethyl)-1-methyl-1H-[1,2,3]triazoleHCID 674863248-Fluoro-7-(trifluoromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 9978854Imidazo[1,2-a]pyridine,8-fluoro-3-[4-fluoro-3-[(1-methyl-1h-1,2,3-triazol-4-yl)methoxy]phenyl]-7-(trifluoromethyl)-

Procedure

8-Fluoro-7-trifluoromethylimidazo[1,2-α]pyridine was coupled to 4-(5-bromo-2-fluorophenoxymethyl)-1-methyl-1H-[1,2,3]triazole as described in Example 6 to give 8-fluoro-3-[4-fluoro-3-(1-methyl-1H-[1,2,3]triazol-4-ylmethoxy)phenyl]-7-trifluoromethylimidazo[1,2-α]pyridine as an off-white solid: δH (400 MHz, d6-DMSO) 4.07 (3H, s), 5.53 (2H, s), 7.14 (1H, dd, J 7 and 7), 7.29-7.31 (1H, m), 7.44 (1H, dd, J 11 and 8), 7.73 (1H, dd, J 8 and 2), 8.06 (1H, s), 8.23 (1H, s), 8.62 (1H, d, J 7); m/z (ES+) 410 [MH+].

Sources & evidence

ORD record
ord-04c46b737ffd44798b8bf73989cf291a
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

Loading…