[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH2:10])[CH:6]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=2)[N:4]=1A solution of nitrile 26I (420 mg, 1.5 mmol) in diethyl ether (30 mL) was added in small amounts to a mixture of LiAlH4 (115 mg, 2 mol eq) in diethyl ether (20 mL) stirred at 0° C. After the addition was completed, the mixture was stirred at room temperature overnight. The excess of LiAlH4 was destroyed at 0° C. by addition of small amount of water (30 mL), the solid formed was filtered off and the organic filtrate was separated, washed with brine (50 mL) and dried over Na2SO4. The organic phase was evaporated under reduced pressure to afford 27I as a pale yellow oil (370 mg, 88% yield). 1HNMR (DMSO, 200 MHz) δ 4.13 (s, 3H), 4.22 (s, 2H), 7.56 (s, 1H), 7.88 (d, 2H, J=7.8), 8.26 (s, 1H), 8.51 (d, 2H, J=8).
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