[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([F:18])[C:15]=2[CH:16]=[O:17])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+].C(Cl)Cl>C1COCC1.O>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([F:18])[C:15]=2[CH2:16][OH:17])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]To the solution of 2-chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile (45 mg, 0.17 mmol) in THF (3 mL) and water (1 mL) was added sodium borohydride (6.5 mg, 0.17 mmol) at 0° C. This reaction mixture was stirred for 0.5 h at room temperature. After addition of CH2Cl2, the organic layer was washed with saturated NaCl solution and extracted with DCM for five times. The combined extracts were dried over Na2SO4, filtered, and evaporated. The resulting mixture was passed through a pad of silica gel, rinsed with 0-50% EtOAc/heptane, and evaporated to give 2-Chloro-4-(5-fluoro-4-hydroxymethyl-pyridin-3-yl)-benzonitrile (21 mg, 46%) as a white solid. ESI-MS m/z: 263 [M+1]+, Retention time 1.11 min. 1H-NMR (CDCl3, 400 MHz) δ 4.56 (s, 2H), 7.66 (dd, J=8.4, 1.6 Hz, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.93 (d, J=8.4 Hz, 1H), 8.39 (s, 1H), 8.55 (s, 1H).
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