[Br:1][C:2]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])C2C(=CC=CC=2)C=1.C(C=C)=O.BrBr.[NH:22]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28]S(N)(=O)=O)[CH2:23]1.C(OC(=O)NC[C@H]1CCNC1)(C)(C)C.[Br:47]C1C=CC2C(=CC=CC=2)N=1.N1C=CC=CC=1OC>>[C:12]([C:10]1[CH:28]=[C:27]2[C:23](=[C:2]([Br:1])[CH:11]=1)[N:22]=[CH:26][C:25]([Br:47])=[CH:24]2)([CH3:15])([CH3:14])[CH3:13]6-tert-butyl-3,8-dibromoquinoline (180) is prepared from 2-bromo-4-tert-butyl naphthalene using acrolein and bromine in accord with the procedure in step 2 of example 7. Introduction of 1-pyrrolidin-3-ylmethyl methansulfonamide moiety can be carried out with (S)-1-pyrrolidin-3-ylmethyl-carbamic acid tert-butyl ester in accord with the procedures in steps 1 to 3 of example 19. Introduction of the pyridine ring is carried out by a Suzuki condensation of the bromoquinoline intermediate with 115 in accord with the procedure in step 2 of example 24 and subsequent demethylation of the methyl pyridinyl ether in accord with the procedure in step 6 of example 22 to afford I-60.
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