[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[C:17]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[NH:19][CH:20]=1)=O)C>C1(C)C=CC=CC=1.O1CCCC1>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[NH:19][CH:20]=[C:16]([CH2:14][OH:13])[C:17]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:26][CH:25]=1121.4 ml (121.4 mmol) of a 1M solution of diisobutylaluminium hydride in toluene were slowly added dropwise to a solution of 12.56 g (40.47 mmol) of 4-ethoxycarbonyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole [which was obtained in step (i) above] in 630 ml of tetrahyrofuran with ice-cooling. After completing the addition, the cooling bath was removed and the mixture was stirred at room temperature for 5 hours. At the end of this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure to give 10.80 g (yield 99%) of the title compound as a pale orange powder.
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