2-(5-Bromo-2-fluorophenyl)nicotinonitrile → 2-[2-Fluoro-5-(8-fluoro-7-trifluoromethylimidazo[1,2-alpha]pyridin-3-yl)phenyl]-nicotinonitrile

HRID 1180319Notes

Reaction equation

HRID 1180319 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]([C:22]2[N:29]=[CH:28][CH:27]=[CH:26][C:23]=2[C:24]#[N:25])[CH:21]=1>>[F:30][C:19]1[CH:18]=[CH:17][C:16]([C:12]2[N:4]3[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:10])[F:11])=[C:2]([F:1])[C:3]3=[N:14][CH:13]=2)=[CH:21][C:20]=1[C:22]1[N:29]=[CH:28][CH:27]=[CH:26][C:23]=1[C:24]#[N:25]

Participants

3

Reactant 2

HCID 222852972-(5-Bromo-2-fluorophenyl)nicotinonitrileHCID 674863248-Fluoro-7-(trifluoromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 104760892-[2-Fluoro-5-(8-fluoro-7-trifluoromethylimidazo[1,2-alpha]pyridin-3-yl)phenyl]-nicotinonitrileYield 45.5%

Procedure

8-Fluoro-7-trifluoromethylimidazo[1,2-α]pyridine (102 mg, 0.5 mmol) and 2-(5-bromo-2-fluorophenyl)nicotinonitrile (208 mg, 0.75 mmol) were coupled following the procedure given in Example 6 to afford 2-[2-fluoro-5-(8-fluoro-7-trifluoromethylimidazo[1,2-α]pyridin-3-yl)phenyl]-nicotinonitrile (91 mg, 45%) as a white solid: δH (360 MHz, CDCl3) 6.98 (1H, dd, J 7 and 6), 7.44-7.54 (2H, m), 7.67-7.72 (1H, m), 7.79 (1H, dd, J 7 and 2), 7.88 (1H, s), 8.15 (1H, dd, J 7 and 2), 8.24 (1H, d, J 7), 8.95 (1H, d, J 2); m/z (ES+) 401 (100%, [MH]+).

Sources & evidence

ORD record
ord-8d93e5c5786e4c8d82a4773fe9dc09ce
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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