2,4-Dichloropyridine → HCID 10318215, compound
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].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=2[C:24]#[N:25])[CH:17]=1.FC1C=CC(B2OC(C)(C)C(C)(C)O2)=C(C=1)C#N.ClC1C=C(Cl)C=CN=1>>[F:30][C:27]1[CH:28]=[CH:29][C:22]([C:18]2[CH:17]=[C:16]([C:12]3[N:4]4[CH:5]=[CH:6][C:7]([C:8]([OH:11])([CH3:10])[CH3:9])=[C:2]([F:1])[C:3]4=[N:14][CH:13]=3)[CH:21]=[CH:20][N:19]=2)=[C:23]([CH:26]=1)[C:24]#[N:25]Participants
Procedure
2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 2-(4-chloropyridin-2-yl)-5-fluorobenzonitrile (prepared from 5-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile and 2,4-dichloropyridine by an analogous procedure to that described in WO 02/076983), by the method of Example 23, to give 5-fluoro-2-{4-[8-fluoro-7-(2-hydroxyprop-2-yl)imidazo[1,2-α]pyridin-3-yl]pyridin-2-yl}benzonitrile: δH (500 MHz, CDCl3) 1.75 (6H, s), 2.08 (1H, s), 7.32 (1H, t, J 7.0), 7.45-7.49 (1H, m), 7.53-7.56 (2H, m), 7.92 (1H, s), 7.98 (1H, t, J 0.7), 7.99 (1H, dd, J 3.4, 5.4), 8.50 (1H, d, J 7.3), 8.87 (1H, d, J 5.1); m/z (ES+) 391. Also isolated from the above reaction was 5-fluoro-2-{4-[8-fluoro-7-(2-hydroxyprop-2-yl)imidazo[1,2-α]pyridin-3-yl]pyridin-2-yl}benzamide: δH (500 MHz, DMSO) 1.59 (6H, s), 7.35-7.44 (3H, m), 7.60 (1H, t, J 0.6), 7.66 (1H, dd, J 0.5, 0.7), 7.82-7.84 (1H, m), 7.85 (1H, s), 7.95 (1H, s), 8.05 (1H, s), 8.60 (1H, d, J 7.1), 8.73 (1H, d, J 5.4); m/z (ES+) 409.
Sources & evidence
- ORD record
- ord-0596971a3dec4a81b1ec4928af42b6dd
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07226926B2
Reaction notes
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