Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CC(C)([O-])C.[Na+]>O1CCOCC1.CCOCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][S:10]([C:4]1[CH:3]=[C:2]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])(=[O:12])=[O:11]A mixture of 4-bromo-2-methanesulfonyl-1-methoxy-benzene (0.65 g,), piperazine (0.43 g,), sodium tert-butoxide (0.13 g) BINAP (19 mg) and [Pd2(dba)3 (27 mg) in dioxane (5 ml) was heated under argon at 100° C. for 24 h. After cooling to room temperature, the reaction mixture was taken up in Et2O (40-50 ml) and washed with brine (15-20 ml). The organic fraction was dried (MgSO4), filtered and evaporated to dryness. The crude material was purified by flash chromatography on silica gel using CH2Cl2:MeOH (9:1 (v/v)) Yield 0.14 g: MS m/z (rel. intensity, 70 eV)) 270 (M+, 23), 229 (11), 228 (bp), 148 (7), 56 (17).
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