C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([C:17]([OH:19])=O)=[CH:15][N:16]=2)[CH:13]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:24]#[N:25].CCN(C(C)C)C(C)C>ClCCl.ClCCCl.CN(C=O)C>[C:24]([C:23]1[CH:26]=[CH:27][C:28]([CH3:29])=[C:21]([NH:20][C:17]([C:14]2[N:12]3[CH:13]=[C:8]([F:7])[CH:9]=[CH:10][C:11]3=[N:16][CH:15]=2)=[O:19])[CH:22]=1)#[N:25]Oxalyl chloride (10 mL, 110 mmol) was added dropwise to a stirred suspension of 6-fluoroimidazo[1,2-a]pyridine-3-carboxylic acid (24b) (2 g, 11 mmol) and catalytic amounts of DMF in dichloromethane (20 mL). After 5 hours, the solvent was evaporated and the solid was suspended in dry DCE (20 mL) and added to a stirred solution of 3-amino-4-methylbenzonitrile (1.45 g, 11 mmol) and DIEA (6 mmol) in DCE (10 mL) at 0° C. After the addition, the reaction was heated at 60° C. for 5 hours. The mixture was subjected to standard aqueous work and silica purification to give N-(5-cyano-2-methylphenyl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide (39) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 10.14 (s, 1H), 9.45 (dd, J=5.2, 2.0 Hz, 1H), 8.62 (s, 1H), 7.90-7.87 (m, 2H), 7.68-7.63 (m, 1H), 7.53 (d, J=8.0 Hz, 1H), 2.37 (s, 3H). MS m/z 295.1 (M+1)+.
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