1-Methyl-1H-indazole-3-carboxaldehyde

b) 1-Methyl-lH-indazole-3-carbaldehyde; (1-Methyl-lH-indazol-3-yl) methanol (0.320 g, 1.97 mmol, from step a above) was dissolved in 25 mL of DCM and Dess-Martin periodinane (0.920 g, 2.17 mmol) was added. The mixture was stirred for 30 min after which 150 mL of diethyl ether was added and the suspension was hydrolyse by addition of 50 ml of 2M NaOH and stirring for 10 min. The ether layer was washed with 1M NaOH and water, dried over Na2SO4, filtered and evaporated. The crude product was chromatographed on a pre-packed Si02-column (Isolute, 10 g) eluted with DCM: MeOH 98: 2. Yield: 0.271 g (86percent). 'H NMR (300 MHz, CDC13) 8 10.21 (s, 1H), 8.29 (m, 1H), 7.50-7. 43 (m, 2H), 7.36 (m, 1H), 4.18 (s, 3H).A solution of NaCN (386 mg, 7.875 mmol) in H2O (1 mL) was added to a solution of General procedure: To a solution of (53 mg, 0.17 mmol, 1.0 eq) and 1-methyl-1H-imidazole-2-carbaldehyde (28 mg, 0.25 mmol, 1.5 eq) in THF (2 mL) under a N2 atmosphere was added NaBH(OAc)3 (72 mg, 0.34 mmol, 2.0 eq) and the mixture was stirred at RT overnight. The mixture was purified by C18 reverse phase column (Biotage, 30% to 70% ACN in water, 0.1% TFA) to afford the title compound (22 mg, 34%) as a white solid. LCMS: [M+H]+ 384.2. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=8.4 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.41 (s, 2H), 7.20 (s, 1H), 4.78 (s, 2H), 3.98 (s, 3H), 3.80 (s, 2H), 3.40 (m, 2H), 3.17-3.00 (m, 3H), 2.59 (s, 3H), 2.24 (m, 2H), 1.95 (m, 2H).

Molecular Weight:160.17
XLogP3:1.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:160.063662883
Monoisotopic Mass:160.063662883
Topological Polar Surface Area:34.9
Heavy Atom Count:12
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes