C([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15](Br)=[C:14]2[C:10]=1[C:11]([CH2:21][C:22]([NH:24][CH3:25])=[O:23])=[CH:12][N:13]2[CH3:20])C1C=CC=CC=1.N1C=CC=CC=1.Cl>CO.[Pd]>[F:18][C:17]1[C:9]([OH:8])=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:20])[CH:12]=[C:11]2[CH2:21][C:22]([NH:24][CH3:25])=[O:23]
A mixture of 33-5 (1.4 g, 4.5 mmol), pyridine (2 mL) and Pd/C (140 mg, 10%) in methanol (20 mL) was stirred at room temperature overnight under hydrogen atmosphere. The mixture was adjusted with hydrochloric acid to pH=5-6. The solid was filtered off and the filtrate was concentrated. The resulting residue was partitioned between water (20 mL) and ethylacetate (20 mL). The organic layer was separated, washed with brine (3×30 mL), dried over MgSO4, filtered and evaporated to obtain 33-6 (700 mg, 85%) as a brown solid. LRMS: calc 236.1 and found: 237.1 [M+1].
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