C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.CCCCCC>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[CH:7][C:6]([CH:5]=[CH:4][CH2:3][OH:2])=[CH:11][CH:10]=2)=[CH:13][CH:14]=1520 mg (2 mmol) of 3-(6-(4-fluorophenyl)pyridin-3-yl)acrylic acid methyl ester were dissolved in 40 ml of dichloromethane and cooled to −70° C. Under argon, 4.65 ml of a 1M solution of diisobutylaluminum hydride in hexane were slowly added. The mixture was stirred at −70° C. for 3 h, quenched with a solution of sodium sulfate, and warmed to room temperature. After filtration over Celite, the organic phase was separated and evaporated. Yield: 430 mg (93%)
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