[CH3:1][C:2]1[CH:3]=[C:4]([S:9]([C:11]2[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=2[C:13]#[N:14])=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH3:20].CCOC(C)=O>CO>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:11]([S:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[O:10])[C:12]=1[C:13]#[N:14]2-[(3,5-Dimethylphenyl)sulfinyl]-6-fluorobenzonitrile (Example 19) (0.4 g, 1.5 mmol) was dissolved in 40 ml of methanol and chilled to -78° C. Condensed ammonia (20 ml, 15.4 g, 905 mmol) was added and the mixture was heated to 150° C. in a sealed Parr bomb for 24 h. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 0.24 g (61%) of 2-amino-6-[(3,5-dimethylphenyl)sulfinyl]benzonitrile: mp 190°-191° C.; NMR (Me2SO-d6, 200 MHz) δ 2.32 (s, 6H), 6.48 (br s, 2H), 6.90 (apparent d, 1H), 7.11 (apparent d, 1H), 7.20 (m, 1H), 7.32 (m, 2H), 7.52 (apparent t, 1H); mass spec (CI) M+ +1=271. Anal. Calc. for C15H14N2OS: C, 66.64; H, 5.22; N, 10.36; S, 11.86. Found: C, 66.71; H, 5.27; N, 10.32; S, 11.84.
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