2-AMINO-4-BROMOQUINOLINE

2-Aminoquinolin-4-ol (0.7 g, 4.37 mmol) was taken up in a pressure tube and treated with phosphorous oxybromide (2.51 g, 8.74 mmol) and phosphorous tribromide (3 mL, 31.8 mmol). The tube was capped under NStep 2: 2-Methyl-2-propanyl 4-(6-(2-(bis(((2-methyl-2-propanyl)oxy)carbonyl)amino)-4-quinolinyl)-5-chloro-7-fluoro-2, 1-benzothiazol-3-yl)-1-piperazinecarboxylate A solution of di-tert-butyl (4-bromoquinolin-2-yl)-2-imidodicarbonate (19.2 mg, 0.045 mmol, prepared in analogous fashion to bis(2-methyl-2-propanyl) (1-bromo-3-isoquinolinyl)-2-imidodicarbonate in Example 26 using (0660) 2-amino-4-quinolinol (60 mg, 0.37 mmol) was stirred in PBr3 (5 mL) at 90 °C overnight. The reaction was then quenched with saturated sodium carbonate solution and extracted with ethyl acetate (50 mLx3). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (eluent: dichloromethane/ethyl acetate, 10-100percent) to give the title compound as a white solid (46 mg, (0661) 56percent). 1H NMR (400 MHz, chloroform-c ) delta 7.99 (ddd, J= 8.3, 1.5, 0.7 Hz, 1H), 7.64 (ddd, J = 8.4, 1.5, 0.6 Hz, 1H), 7.60 (ddd, J = 8.3, 6.6, 1.4 Hz, 1H), 7.35 (ddd, J = 8.2, 6.6, 1.5 Hz, 1H), (0662) 7.08 (s, 1H).2-Aminoquinolin-4-ol (0.7 g, 4.37 mmol) was taken up in a pressure tube and treated with phosphorous oxybromide (2.51 g, 8.74 mmol) and phosphorous tribromide (3 mL, 31.8 mmol). The tube was capped under N2 and heated at 150 C for 19 h. The reaction mixture was then cooled to room temperature and basified using aq. NaOH (2 M, 10 mL) and extracted with ethyl acetate (3 x 25 mL). The combined organic layers were washed with water (20 mL), dried over Na2S04 and evaporated under reduced pressure. The solid obtained was washed with hexane (20 mL) to remove any nonpolar impurity and dried under reduced pressure to afford a dark brown residue which was purified by column chromatography on silica (using a gradient of methanol and chloroform) to afford To a solution of Example 4 Preparation of 4-(1H-pyrrolo[2, 3-b]pyridin-3-yl)quinolin-2-ylamine (A1) 0.42 ml (3.00 mmol) of triethylamine and 0.22 ml (1.5 mmol) of 4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane are added successively to a solution, kept under argon, of 35 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium and 344 mg (1.00 mmol) of tert-butyl 3-iodopyrrolo[2, 3-b]pyridine-1-carboxylate in 5 ml of dioxane, and the mixture is stirred at 80° C. for 3 hours under argon. The reaction mixture is cooled to room temperature; 5 ml of methanol, 223 mg (1.0 mmol) of

Molecular Weight:223.07
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:221.97926
Monoisotopic Mass:221.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes