ChemicalBook CAS DataBase List 1-METHYL-1H-INDAZOLE-3-CARBALDEHYDE

1-METHYL-1H-INDAZOLE-3-CARBALDEHYDE synthesis

3synthesis methods

Product Name:1-METHYL-1H-INDAZOLE-3-CARBALDEHYDE
CAS Number:4002-83-9
Molecular formula:C9H8N2O
Molecular Weight:160.17

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4002-83-9
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$56.00/250mg

Yield: 86%

Reaction Conditions:

Stage #1:(1-methyl-1H-indazol-3-yl)methanol with Dess-Martin periodane in dichloromethane for 0.5 h;
Stage #2: with sodium hydroxide;water in diethyl ether;dichloromethane for 0.166667 h;

Steps:

b
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 (86%). '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).

References:

ASTRAZENECA AB WO2005/66132, 2005, A1 Location in patent:Page/Page column 45-46