3-Bromo-1H-pyrazolo[4,3-c]pyridine

Into a 100 mL round-bottom flask, was placed a solution of 3-bromo-1H-pyrazolo[4, 3-cjpyridine (2.45 g, 23.34 mmol, 1.0 eq) in DMF (40 mL), (5)-tert-butyl 3-(tosyloxy)piperidine-1-carboxylate (5.06 g, 14.48 mmol, 1.2 eq), and Cs2CO3 (6.1 g, 18.55mmol, 1.5 eq). The resulting solution was stirred for 12 h at 65 C. and then quenched by theaddition of 100 mL of water. The resulting solution was extracted with EA (80 mL*3) andthe organic layers combined. The organics were washed with brine, dried over anhydrous Na2CO3, The solvent were removed under vacuum and the residue was purified by silica gel column chromatography (DCM/MeOH=200: 1 - 100:1) to give the title product (3.5 g, yield 76.9 %). 'H-NMR ( 400 MHz, CDC13): oe 8.98 (s, 1H), 8.50 (d, J= 4.8 Hz, 1H), 7.32 (d, J=5.6 Hz, 1H), 3.91 (s, 1H), 3.76-3.80 (m, 2H), 3.53-3.59 (m, 1H), 2.59 (s, 1H), 2.38-2.44(m, 1H), 1.48 (s, 9H). LCMS: m/z = 367 [M+Hf.Into a 100 mL round-bottom flask, was placed a solution of 3-bromo-1H- pyrazolo[4, 3-cjpyridine (3) (2 g, 10 mmol) in DMF (20 mL), (S)-tert-butyl 3- (tosyloxy)piperidine-1-carboxylate (4.3 g, 12 mmol), and Cs2CO3 (5.9 g, 18 mmol). The resulting solution was stirred for 24 h at 65 C. and then quenched by the addition of 100 mL of water. The resulting solution was extracted with EA and the organic layers combined. Theorganics were washed with brine, dried over anhydrous NaHCO3, The solvent were removed under vacuum and the residue was purified by column chromatography on silica gel (gradient:DCM/MeOH=200:i 100:1) to give the title product (0.8 g, yield 21.0 %). 'HNMR (400 MHz, CDC13): oe 8.97 (s, 1H), 8.48 (d, J 5.6 Hz, 1H), 7.36 (d, J 5.6 Hz, 1H), 4.43-4.38 (m, 3H), 3.2 (br, 1H), 2.88-2.81 (m, 1H), 2.30-2.17 (m, 2H), 1.95-1.91 (m, 1H), 1.72-1.62 (m, 1H), 1.46 (s, 9H). LCMS: m/z = 382 [M+Hf

Molecular Weight:198.02
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:41.6
Heavy Atom Count:10
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes