6-Bromo-4-methylquinoline

Stir a solution OF 4-BROMO-PHENYLAMINE (1 EQ), in 1, 4-dioxane and cool to approximately 12 C. Slowly add sulfuric acid (2 eq) and heat at reflux. Add methylvinyl ketone (1.5 eq) dropwise into the refluxing solution. Heat the solution for 1 hour after addition is complete. Evaporate the reaction solution to dryness and dissolve in methylene chloride. Adjust the solution to pH 8 with 1 M sodium carbonate and extract three times with water. Chromatograph the residue on SI02 (70/30 hexane/ethyl acetate) to obtain the desired subtitled INTERMEDIATE. MS ES+ M/E = 158. 2 (M+1).Compound 14a (500 mg, 2.25 mmol) was dissolved in 50 mL of tetrahydrofuran. The reaction solution was added dropwise with diisopropylamino lithium (723.54 mg, 6.75 mmol) at -78C, and stirred for 1 hour. The reaction solution was added with methyl iodide (3.20 g, 22.51 mmol), gradually warmed up to room temperature, and stirred overnight. The reaction solution was added with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate three times. The organic phases were combined, washed with saturated sodium chloride solution once, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by CombiFlash rapid preparation instrument with elution system B to obtain the title product 44a (480 mg), yield: 90.3%.

Molecular Weight:222.08
XLogP3:3.3
Hydrogen Bond Acceptor Count:1
Exact Mass:220.98401
Monoisotopic Mass:220.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes