, three.70 (s, 3H); MS ESI (m/z): 400.4 (M+H) +, calc. 399. HRMS (EI) m / z calcd for C24H21N3O3Na (M+Na)+ 422.1475, located 422.1476.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript5-(3-(1H-Indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-amine (9) NMR (DMSO-d6, 300 MHz): 11.73 (d, J = 1.eight Hz, 1H), 11.05 (s, 1 H), eight.43 (d, J = 2.4 Hz, 1H), eight.29 (d, J = 1.8 Hz, 1H), 8.27 (d, J = two.1 Hz, 1H), 7.88 (s, 1H), 7.76 (dd, J = 2.4, 8.4 Hz, 1H), 7.46 (s, 2H), 7.33 (m, 1H), six.55 (dd, J = 0.six, 8.7 Hz, 1H), 6.46 (m, 1 H), five.99 (s, two H). HPLC retention time: 1.ten minutes. MS ESI (m/z): 326.two (M+H)+, calc. 325. HRMS (EI) m / z calcd for C20H16N5 (M+H)+ 326.1400, found 326.1401.1H5-(5-(3,4,5-Trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-amine (10)1HNMR (DMSO-d6, 300 MHz): 11.82 (s, 1H), 8.53 (d, J = 1.8 Hz, 1H), 8.31 (d, J = 1.8, 1 H), eight.28 (d, J = 1.five Hz), 7.76 (dd, J = two.1, eight.4 Hz, 1 H), 7.70 (d, J = two.4 Hz, 1H), 6.95 (s, 2H), 6.54 (d, J = eight.4 Hz, 1 H), 5.87 (s, 2H), three.86 (s, 6H), three.68 (s, 3H); MS ESI (m/z): 377.four (M+H), calc. 376. HRMS (EI) m / z calcd for C21H21N4O3 (M+H)+ 377.1608, discovered 377.1607.5-(3-(1H-Indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyrimidin-2-amine (11) MS ESI (m/z): 327.2 (M+H), calc. 326; HRMS (EI) m / z calcd for C19H15N6 (M+H)+ 327.1353, discovered 327.1354. 5-(5-(three,four,5-Trimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine (12) MS ESI (m/z): 378.Halocarban Biological Activity four (M+H), calc. 377; HRMS (EI) m / z calcd for C20H20N5O3 (M+H)+ 378.1561, discovered 378.1563. 5-(5-(4-((4-Methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1Hpyrrolo[2,3b]pyridine (13) To a resolution of 23 (four.00 g, five.46 mmol) in MeOH (20 mL) was added NaOH (723 mg, 16.4 mmol). The resulting mixture was heated at 50 for 60 min. Following completion on the reaction, the item was extracted utilizing 250 mL IPA:CHCl3 (1:3) and water. The organic portions had been dried and concentrated in vacuo. The crude solution was purified on a silica gel column to afford 13 (1.57 g, 68 ). 1H NMR (DMSO-d6, 300 MHz): 11.96 (s, 1H), 11.63 (s, 1H), eight.61 (d, J = 1.5 Hz, 1H), eight.56 (d, J = 1.2 Hz, 1H), 8.41 (d, J = 0.9 Hz, 1H), 8.31 (d, J = 1.two Hz, 1H), 7.89 (d, J = 1.5 Hz, 1H), 7.73 (d, J = four.8 Hz, 2H), 7.49 7.48 (m, 1H), 7.40 (d, J = 4.eight Hz, 2H), 6.51 6.49 (m, 1H), three.49 (s, 2H), two.38 2.36 (m, 4H), 2.21 (s, 3H); ESI (m/z) 423.four (M+H)+, calc. 422; HRMS (EI) m / z calcd for C26H27N6 (M+H)+ 423.2292, located 423.2295. 5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (15) Within a 3 liter round bottom flask 5-bromo-1H-pyrrolo[2,3-b]pyridine (63g, 319 mmol) was dissolved in acetone 1500 mL. To the stirred mixture was added NIS (79.1g, 351 mmol) andJ Med Chem. Author manuscript; readily available in PMC 2014 October 24.S2116 medchemexpress Goodfellow et al.PMID:24631563 Pagethe resulting mixture was stirred for 1.five hour; the precipitated solid was collected by filtration and washed with cold acetone (400mL) to afford 15 (89.8 g, 88 yield) as white strong. 1H NMR (DMSO-d6, 300MHz) 12.35 (bs, 1H), eight.31 (d, J = 1.five Hz, 1H), 7.86 (dd, J = 1.2 Hz, 0.3 Hz, 1 H), 7.80 (d, J = 1.5 Hz, 1H); MS ESI (m/z): 322/324 (M+H)+, calc. 323. 5-Bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (16) To a stirred answer of 15 (45.0g, 139 mmol) in 700 mL of anhydrous THF cooled to 0 with an ice bath was added NaH [60 dispersion in mineral oil] (eight.three g, 208 mmol). The reaction mixture was stirred for 20 min at 0 , right after which p-toluenesulfonyl chloride (29.1 g, 153 mmol) was added. The resulting mixture was stirred at 0 for 1.five hr, following conf.
