4-(5-bromo-2-fluorophenoxymethyl)-1-methyl-1H-[1,2,3]triazole → 2-{8-fluoro-3-[4-fluoro-3-(1-methyl-1H-[1,2,3]triazol-4-ylmethoxy)phenyl]imidazo[1,2-alpha]pyridin-7-yl}propan-2-ol

HRID 1180266Notes

Reaction equation

HRID 1180266 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]([OH:11])([CH3:10])[CH3:9].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]([OH:11])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 179648304-(5-bromo-2-fluorophenoxymethyl)-1-methyl-1H-[1,2,3]triazoleHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 100238502-{8-fluoro-3-[4-fluoro-3-(1-methyl-1H-[1,2,3]triazol-4-ylmethoxy)phenyl]imidazo[1,2-alpha]pyridin-7-yl}propan-2-ol

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 4-(5-bromo-2-fluorophenoxymethyl)-1-methyl-1H-[1,2,3]triazole as described in Example 6 to give 2-{8-fluoro-3-[4-fluoro-3-(1-methyl-1H-[1,2,3]triazol-4-ylmethoxy)phenyl]imidazo[1,2-α]pyridin-7-yl}propan-2-ol as an off-white solid: δH (400 MHz, d6-DMSO) 1.58 (6H, s), 4.07 (3H, s), 5.35 (2H, s), 5.55 (1H, s), 7.16-7.23 (2H, m), 7.37 (1H, dd, J 11 and 9), 7.65 (1H, dd, J 8 and 2), 7.76 (1H, s), 8.21 (1H, s), 8.43 (1H, d, J 7); m/z (ES+) 400 [MH+].

Sources & evidence

ORD record
ord-3178203ff3df4ef6820f03fc5091bd02
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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