2-Bromo-1-[4-(dimethylamino)phenyl]ethanone

In 30 ml of THF was dissolved 2 (5.1 g, 1 eq), then at 0° C. was added dropwise a mixture of diethylphosphite (2.04 ml, 1 eq) and EtTo 13 tetrahydrofuran (40 mL) was added 14 2, 2-dibromo-1-(4-(dimethylamino)phenyl)ethanone (6.84 g, 21.5 mmol) synthesized in the step 1-1, to which was then slowly added a solution of 15 diethyl phosphite (3 mL) and 16 triethylamine (3.2 mL) in tetrahydrofuran (25 mL) at 0° C. through a dropping funnel. The resultant was stirred at room temperature for 11 hours. The solvent was distilled off under reduced pressure for concentration, and the residue was added to 10 water cooled with ice, which was then stirred for 0.5 hour. The resultant solid was collected by filtration and washed with water cooled with ice to provide (17 2) in the scheme 1 (yield: 3.38 g (65.5percent)). [0051] . To a stirred solution of 83-1 (1.76 g, 5.60 mmol) in THF (10 mL) was added the solution of (EtO)6-Bromo-2-(4'-Dimethylamino-)Phenyl-Imidazo [1, 2-a] pyridine (17) A mixture of 2-bromo-4'-dimethylaminoacetophenone, (968 mg, 4 mmol) and 2-amino-5-bromo-pyridine (692 mg, 4 mmol) in EtOH (25 mL) was stirred under reflux for 2 hr. NaHCO3 (500 mg) was added after the mixture was cooled down. The resulting mixture was stirred under reflux for 4.5 hr. The mixture was cooled down, filtered to give 655 mg of product, 17 (52%).General procedure: The suspension of bromide 6 (8.0mmol, 1.0 eq) and thiol (8.0mmol, 1.0 equiv.) in anhydrous EtOH (30mL) was stirred at 90C for 18h. The reaction mixture was cooled to room temperature and the forming precipitate was filtered off, yielding the pure product. If necessary, the product was purified by flash chromatography.General procedure: To a stirred suspension of benzo [d]oxazol-2(3H)-one derivative, or benzimidazole, or 2H-benzo [b] [1, 4]oxazin-3(4H)-one(1.0 mmol), anhydrous K2CO3 (1.2 mmol) was added in the DMFsolvent for 20 min at 70 C. Then bromoacetylated 1a-1f or 2a-2c(1.3 mmol) and TBAI (0.1 mmol) were added simultaneously. Thereaction was stirred and heated for 4 h. After completion, themixture was extracted with EtOAc/H2O three times. The combinedorganic layers were washed with brine, dried over anhydrousNa2SO4, filtered and concentrated under reduced pressure. Thecrude product was purified by silica gel column chromatographyeluting with EtOAc/PE (3:1e8:1) to afford compounds B01-B29, C01-C03.

Molecular Weight:242.11
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:241.01023
Monoisotopic Mass:241.01023
Topological Polar Surface Area:20.3
Heavy Atom Count:13
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes