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. 2023 Jan 10;66(2):1157–1171. doi: 10.1021/acs.jmedchem.2c01521

Scheme 3. Synthesis of Quinoline 7 and Naphthyridines 8–12.

Scheme 3

Reagents and conditions: (A) a) (1-methyl-1H-pyrazol-4-yl)methanamine or (5-methyl-1,3,4-thiadiazol-2-yl)methanamine, DIPEA, NMP, 100–140 °C, 3–16 h, 45%–72%; b) I-3, [1,1′-binaphthalen]-2-yldi-tert-butylphosphane, Pd(OAc)2, Cs2CO3, toluene, 80 °C, 15 h, 31% (7); or I-3, Josiphos SL-J009-1, Pd2(dba)3, Cs2CO3, toluene, 140–160 °C, 0.5–15 h, 19%–51% (9, 11, 12); (B) c) I-3 (racemic), [1,1′-binaphthalen]-2-yldi-tert-butylphosphane, Pd(OAc)2, Cs2CO3, toluene, 80 °C, 1.5 h, 47% (I-17); d) I-3, triphenylphosphine, DIAD, THF, rt, 5 min, 37% (I-19); e) (1-methyl-1H-pyrazol-4-yl)methanamine, DIPEA, NMP, 100 °C, 48 h, 80% (8); f) (1-methyl-1H-pyrazol-4-yl)methanamine, DavePhos, Pd2(dba)3, NaOtBu, toluene, 120 °C, 40 min, 76% (10).