Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.ClCCl.C(=O)([O-])[O-].[K+].[K+].[CH:27]1(B(O)O)[CH2:29][CH2:28]1>O1CCOCC1.Cl[Pd-2](Cl)([P+](C1C=CCC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CCC=1>[CH:27]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=2[N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH2:29][CH2:28]1
A mixture of 1-(3-bromo-5-nitro-4-pyridyl)-4-methyl-piperazine (synthesized from 1-methylpiperazine and 3-bromo-4-chloro-5-nitropyridine using procedure Step 1 of Preparation N-1) (467.4 mg, 1.552 mmol), ferrous; dichloro-bis[cyclopenta-1,4-dien-1-yl(diphenyl)phosphaniumyl]palladium(2-); dichloromethane (63.37 mg, 0.07760 mmol), potassium carbonate (429.0 mg, 3.104 mmol) and cyclopropylboronic acid (200.0 mg, 2.328 mmol) in dioxane (5 mL) was degassed and flushed with nitrogen (×2). The reaction was heated at 100° C. in a sealed tube for 18 h. At room temperature the reaction mixture was filtered through Celite and evaporated to dryness, yielding 1-(3-cyclopropyl-5-nitropyridin-4-yl)-4-methylpiperazine as a dark orange solid that was used directly in the next reaction without further purification (288 mg, 66%). MS (ES+) 263.2
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