[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:10][CH3:11])[CH:3]=1.S(C)C.CO.Cl>O1CCCC1.C(OCC)(=O)C.O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([S:10][CH3:11])[CH:3]=1
Under N2, 4-fluoro-2-(methylthio)benzonitrile (1.67 g, 0.1 mol) was dissolved in 20 mL tetrahydrofuran and treated with 10 mL 2M BH3.Me2S. This was heated at 60° C. for 2 hrs. Heating was discontinued and 5 mL MeOH was cautiously added, followed by the cautious addition of 4 mL 6N HCl. Additional H2O (20 mL) was added followed by ethyl acetate. The layers were separated. The aqueous layer was made basic with 1N NaOH and extracted with CH2Cl2. The extracts were dried (MgSO4), filtered, concentrated and dried in vacuo to give 1.3 g of the title compound as a solid (Yield 76%). 1H NMR (500 MHz, CDCl3) δ ppm: 7.20–7.31 (1H, m) 6.90 (1H, dd, J=2.4 Hz) 6.75–6.86 (1H, m) 3.86 (2H, s) 2.47 (3H, s); LC/MS m/z 172.
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