3-Methyl-1H-pyrazolo[4,3-b]pyridine

A solution of 1-(3-fluoropyridin-2-yl)ethanone (1.00 g, 7.19 mmol) in hydrazine monohydrate (12 mL, 247.00 mmol) was heated at 130 °C for 3 h under microwave irradiation. Water (50 mL) was added and the mixture extracted with ethyl acetate (3 x 25 mL). The combined organic layers were dried (MgS04), filtered, and concentrated in vacuo. Purified by Biotage (SNAP 50 g column, ethyl acetate/ethanol 95/5 -> 70/30) to give a cream colored solid (575 mg, 60percent). 1 H NMR (500 MHz, DMSO-d6) δ 12.87 (br s, 1 H), 8.46 (dd, J = 4.3, 1.4 Hz, 1 H), 7.91 (dd, J = 8.5, 1.4 Hz, 1 H), 7.33 (dd, J = 8.5, 4.3 Hz, 1 H), 2.53 (s, 3H). 13C NMR (126 MHz, DMSO-d6) δ 144.51 , 142.04, 139.94, 133.42, 121.12, 118.49, 11.24. LCMS (Method M) Rt 0.52 min, [M+H]+ 134; HRMS calcd. for C7H8N3: 134.0718, found: 134.0726.

Molecular Weight:133.15
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:133.063997236
Monoisotopic Mass:133.063997236
Topological Polar Surface Area:41.6
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes