5-BroMo-6-azaindole

Step 4: 5-bromo-lH-pyrrolo[2, 3-c]pyridineTo the solution of 2-(2-bromo-5-nitropyridin-4-yl)-N, N- dimethylethenamine (62 mg, 0.23 mmol) in AcOH (2 mL), iron (127 mg, 2.28 mmol) was added at room temperature and the mixture was heated at 70 °C for 2 hours. The mixture was cooled, poured into EtOAc (30 mL), filtered through Celite. The filtration was washed with 5percent NaHC0(2) 5-Bromo-1H-pyrrolo[2, 3-c]pyridine Under NThe crude product from above was dissolved in acetic acid (1000 mL), iron (78.0 g, 1400 mmol, 10 eq) was added at room temperature and the mixture was heated to 70° C. for 2 hr, filtered through a celite pad and concentrated under reduced pressure. To a solution of 5-bromo-lH-pyrrolo[2, 3-c]pyridine (3.2 g, 16.24 mmol) in dioxane (60 mL) and water (20.00 mL) solvent mixture were added tert-butyl 4-(4, 4, 5, 5- tetramethyl-l, 3, 2-dioxaborolan-2-yl)-5, 6-dihydropyridine-l(2H)-carboxylate (5.02 g, 16.24 mmol) and potassium phosphate tribasic (10.34 g, 48.7 mmol). The reaction mixture was degassed with nitrogen for 5 min., PdCl2(dppf)-CH2Cl2 adduct (1.326 g, 1.624 mmol) was added, and the reaction mixture was stirred in a sealed tube at 90 C for 3 h. The reaction mass was concentrated, then the residue was diluted with EtOAc (20 mL), the solids were filtered, the filtrate was collected and concentrated to get crude compound. The crude compound was purified by silica gel chromatography on an ISCO instrument using 40 g silica column, the compound was eluted in 15% EA in hexanes, the fractions were collected and concentrated to afford tert-butyl 4-(lH-pyrrolo[2, 3-c] pyridin-5-yl)-5, 6-dihydropyridine-l(2H)-carboxylate (2.5 g, 8.35 mmol, 51% yield) as a pale brown solid. LCMS retention time 0.95 min [L] MS m/z 300.2 [M+H]+.General procedure: To a stirred suspension of 60% NaH (0.146 g, 6.091 mmol) in DMF (20 mL), 5-bromo-1 H-pyrrolo[2, 3-c]pyridine (0.8 g, 4.06 mmol) was added at 0 C and stirred for 15 min. Then, 1-bromo butane (0.66 g, 4.873 mmol) was added to the reaction mixture at 0 C. The resulting mixture was allowed to warm to rt and stirred for 16 h. The reaction mixture was quenched with water and extracted EtOAc and the organic layer was dried over anhydrous Na2S04, and it was concentrated under reduced pressure. The crude compound was purified by flash column chromatography using 10% EtOAc in pet ether as an eluent to afford the title compound (0.78 g, 67%). LC-

Molecular Weight:197.03
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes