4-Fluoro-3-(pyridin-3-yl)benzeneboronic acid → 7-Chloro-8-fluoro-3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

HRID 1180227Notes

Reaction equation

HRID 1180227 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([Cl:12])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][C:15]=1[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>>[Cl:12][C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[C:15]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[CH:16]=3)=[CH:3][N:4]=[C:5]2[C:10]=1[F:11]

Participants

3

Reactant 2

HCID 224735734-Fluoro-3-(pyridin-3-yl)benzeneboronic acidHCID 695617863-Bromo-7-chloro-8-fluoroimidazo[1,2-a]pyridine

Product 1

HCID 100202217-Chloro-8-fluoro-3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridineYield 80%

Procedure

3-Bromo-7-chloro-8-fluoroimidazo[1,2-α]pyridine (45 mg, 0.18 mmol) was coupled with 4-fluoro-3-(pyridin-3-yl)phenylboronic acid (49 mg, 0.19 mmol), as described in Example 1, to afford the title compound as a white amorphous solid (49 mg, 80%): δH (400 MHz, DMSO) 7.10 (1H, t, J 7.0), 7.54-7.61 (2H, m), 7.77-7.81 (1H, m), 7.92 (1H, dd, J 2.3, 7.4), 7.94 (1H, s), 8.09-8.12 (1H, m), 8.52 (1H, dd, J 1.0, 7.2), 8.65-8.66 (1H, m), 8.88 (1H, s); m/z (ES+) 342 (100%, [MH]+).

Sources & evidence

ORD record
ord-4e179e7f4e7f49c3a1a96ea0bebb9957
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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