2,3-DIBROMOQUINOLINE

To a stirred solution of 2-bromoquinoline (306 mg, 1.47 mmol) in CHGeneral procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CHGeneral procedure: Intermediate 3-6 was synthesized according to Scheme 25 below.A solution of 9H-carbazole (20.0 g, 0.120 mol) and 3-bromo-2-iodopyridine (35.7 g, 0.126 mol) in dimethylacetamide [DMAc] (30.4 g, 0.478 mol) of copper powder. The reaction temperature was heated and stirred at 110 DEG C for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then solidified using a large amount of water. The solid obtained by filtration was diluted with ethyl acetate and the solvent was washed twice with ammonia water. The obtained organic layer was dried over anhydrous magnesium sulfate and then concentrated by filtration. The intermediate was purified by a column chromatography to obtain (13.5 g, yield 35%).Intermediate 4-8 was synthesized according to Scheme 35 below.Was reacted under the same conditions as in Synthesis Example 25 to synthesize Intermediate 4-8.General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7-8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.A 100 mL 3 -neck round bottom flask fitted with a magnetic stirrer and flushed with nitrogen was charged with zinc dust (813 mg, preactivated according to the abovePreparation 1, 12.7 mmol, 2.0 eq.) and DMA (10 mL, anhydrous). 1, 2-dibromoethane (236 mg, 1.27 mmol, 0.2 eq) was added slowly, followed by TMSC1 (137 mg, 1.27 mmol, 0.2 eq). The reaction was stirred for 15 min at RT. A solution of N-Boc-3-iodoazetidine (2) (2.7 g, 9.5 mmol, 1.5 eq) in DMA (10 mL, anhydrous) was added dropwise. The suspension was stirred for 1 h at RT.[00314] A 100 mL 3 -neck round bottom flask fitted with a mechanical stirrer was charged with

Molecular Weight:286.95
XLogP3:3.9
Hydrogen Bond Acceptor Count:1
Exact Mass:286.87682
Monoisotopic Mass:284.87887
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes