4-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

4-bromo-2-methyl-1W-pyrrolo[2, 3-b]pyridine To a solution of 4-bromo-2-methyl-1 -(phenylsulfonyl)-1 H-pyrrolo[2, 3-5]pyridine (D9) (16 g, 0.045 mol) in 1 , 4 dioxane (320 mL) was added 2M aqueous sodium hydroxide (114 rmL, 0.228 mol).The reaction was heated to 6OInto a 100-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed To a degassed solution of 4-bromo-2-methyl- 17/-pyrrolo[ 2, 3-b|pyridine (122 mg; 0.578 mmol) in dioxane (3.0 mL) were added potassium acetate (141 mg; 1.45 mmol), 4, 4, 4?, 4?, 5, 5, 5?, 5?-octamethyl- 2, 2?-bi(l, 3, 2-dioxaborolane) (293 mg; 1.156 mmol), (2-dicyclohexylphosphino-2', 6'- dimethoxybiphenyl) [2-(2'-amino-l, -biphenyl)]palladium(II) methanesulfonate (18 mg; 0.023 mmol; CAS: 1445085-82-4) and the mixture was stirred at 90 C for 3.5 hours. The solvent was evaporated in vacuo and the residue was purified by column chromatography (dichloromethane/methanol, 10: 1). The product was obtained as a gray solid (57 mg, 75 % yield; ca. 70 % purity). (0344) NMR (500 MHz, CDCl3) d (ppm) 10.45 (s, 1H), 8.19 (d, 7 = 4.89 Hz, 1H), 7.43 (d, 7 = 4.78 Hz, 1H), 6.60 (s, 1H), 2.55 (s, 3H), 1.40 (s, 12H). (0345) 13C NMR (126 MHz, CDCl3) d (ppm) 148.7, 148.0, 139.2, 137.7, 127.1, 121.6, 100.7, 84.2, 25.1, 14.3. HRMS calculated for Ci4H2oBN202[M+H]+259.l6l5, found 259.1613.A mixture of 4-bromo-2-methyl-1 H-pyrrolo[2, 3-b]pyridine (121 mg, 0.57mmol), 3-(4, 4, 5, 5- tetramethyl-1 , 3, 2-dioxaborolan-2-yl)pyrazolo[1 , 5-b]pyridazine (155mg, 0.63mmol), Brett Phos Pd G3 (23mg, 0.023mmol) and potassium phosphate (243mg, 1.15mmol) in degassed ethanol (3ml_) and water (1.5mL) was heated at 140C for 30 mins in the microwave. After cooling, the mixture was partitioned between ethyl acetate and water and the organic layer was separated, washed with brine, dried (Na2S04) and concentrated in vacuo. The crude product was purified by MDAP (Basic) to afford the title compound as a solid (30mg, 21 %). LCMS (Method 1): Rt 2.24 min, m/z 249.9 [MH+]. 1 H NMR (400 MHz, d6-DMSO): 2.43 (3H, s), 6.32-6.34 (1 H, m), 7.23 (1 H, d, J=5.0 Hz), 7.34 (1 H, dd, J=4.4, 9.1 Hz), 8.17 (1 H, d, J=5.0 Hz), 8.44 (1 H, dd, J=1.8, 9.1 Hz), 8.55-8.57 (2H, m), 1 1.62 (1 H, s).

Molecular Weight:211.06
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:209.97926
Monoisotopic Mass:209.97926
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes