[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:6]([OH:8])=O)#[N:2].[N:13]1([C:18]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[O:19])[CH:17]=[CH:16]N=C1.[BH4-].[Na+].O1CCC[CH2:28]1>O>[F:12][C:10]1[CH:11]=[C:3]([CH:4]=[C:5]([CH2:6][O:8][C:17]2[CH:16]=[C:21]3[N:22]([CH3:28])[CH2:23][CH2:24][N:20]3[C:18](=[O:19])[N:13]=2)[CH:9]=1)[C:1]#[N:2]
To a solution of 3-cyano-5-fluorobenzoic acid (1.00 g, 6.06 mmol) in tetrahydrofuran (THF) (20 mL) was added di(1H-imidazol-1-yl)methanone (1.08 g, 6.66 mmol). The reaction mixture was stirred at 20° C. for 1 h. Then a suspension of NaBH4 (0.687 g, 18.2 mmol) in water (5 mL) was added dropwise. The reaction mixture was stirred at 20° C. for 20 h, quenched with saturated aqueous NH4Cl and extracted with ethyl acetate (20 mL×3). Combined organic portions were washed with saturated aqueous NaHCO3 (20 mL), brine (20 mL), dried over Na2SO4 and concentrated in vacuo to get the desired product as a white solid. 1HNMR (400 MHz, CDCl3): δ 4.697 (m, 2H) & 7.104˜7.400 (m, 3H).
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