2-(5-Bromo-2-fluorophenyl)-3,5-difluoropyridine → 3-[3-(3,5-Difluoropyridin-2-yl)-4-fluorophenyl]-8-fluoro-7-trifluoromethylimidazo[1,2-alpha]pyridine

HRID 1180318Notes

Reaction equation

HRID 1180318 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[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][N:23]=2)[CH:21]=1>>[F:28][C:27]1[C:22]([C:20]2[CH:21]=[C:16]([C:12]3[N:4]4[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:10])[F:11])=[C:2]([F:1])[C:3]4=[N:14][CH:13]=3)[CH:17]=[CH:18][C:19]=2[F:30])=[N:23][CH:24]=[C:25]([F:29])[CH:26]=1

Participants

3

Reactant 2

HCID 116808232-(5-Bromo-2-fluorophenyl)-3,5-difluoropyridineHCID 674863248-Fluoro-7-(trifluoromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 117423323-[3-(3,5-Difluoropyridin-2-yl)-4-fluorophenyl]-8-fluoro-7-trifluoromethylimidazo[1,2-alpha]pyridineYield 32%

Procedure

8-Fluoro-7-trifluoromethylimidazo[1,2-α]pyridine (102 mg, 0.5 mmol) and 2-(5-bromo-2-fluorophenyl)-3,5-difluoropyridine (216 mg, 0.75 mmol) were coupled following the procedure given in Example 6 to afford 3-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]-8-fluoro-7-trifluoromethylimidazo[1,2-α]pyridine (65 mg, 32%) as an off-white solid: δH (360 MHz, CDCl3) 6.97 (1H, dd, J 7 and 6), 7.35-7.42 (2H, m), 7.61-7.65 (1H, m), 7.78 (1H, dd, J 7 and 2), 7.87 (1H, s), 8.16 (1H, d, J 7), 8.49 (1H, d, J 2); m/z (ES+) 412 (100%, [MH]+).

Sources & evidence

ORD record
ord-da1c9cb3f80641b495624b1110f866b0
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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