3-Aminopyridine → HCID 66599414, compound

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[CH:4][C:3]=1[C:16]#[N:17].[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1.CC([O-])(C)C.[K+]>CS(C)=O>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:24][C:20]3[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=3)=[C:3]([C:16]#[N:17])[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

Procedure

To a solution of 4-fluoro-3′-methoxybiphenyl-3-carbonitrile (0.60 g, 2.64 mmol, Example 203A) in DMSO (4 mL) was added pyridine-3-amine (0.27 g, 2.90 mmol) and KOtBu (0.15 g, 1.38 mmol). The reaction stirred under nitrogen at room temperature 12 h. The reaction mixture was partitioned between water and ethyl acetate, the layers were separated, the organics were washed with water, brine solution, dried over Na2SO4 and concentrated to give the crude product. The crude material was purified by silica gel column chromatography (DCM/(2M)NH4-MeOH=100/0−95/5) to afford 0.53 g of 3′-methoxy-4-(pyridine-3-ylamino)biphenyl-3-carbonitrile. MS (ESI) m/z 302.2 (M+H). 1H NMR (MeOD) d ppm 8.43 (1H, d, J=2.75 Hz), 8.19 (1H, dd, J=4.88, 1.22 Hz), 7.91 (1H, d, J=2.14 Hz), 7.81 (1H, dd, J=8.70, 2.29 Hz), 7.56-7.73 (1H, m), 7.32-7.47 (3H, m), 7.11-7.23(2H, m), 6.94(1H, dd, J=8.24, 2.44 Hz), 3.87 (3H, s).