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ChemicalBook CAS DataBase List 3,7-DiMethyl-1H-indazole-5-carboxylic acid
1031417-75-0

3,7-DiMethyl-1H-indazole-5-carboxylic acid synthesis

4synthesis methods
-

Yield:1031417-75-0 17%

Reaction Conditions:

Stage #1: 5-bromo-3,7-dimethyl-1H-indazole;molybdenum hexacarbonylwith sodium carbonate;trans-bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium in 1,4-dioxane;water at 165; for 0.25 h;
Stage #2: with hydrogenchloride in 1,4-dioxane;water; pH=2;

Steps:

10

To a reaction vessel containing a re-purified solution of 5-bromo-3,7-dimethyl-1 H-indazole (prepared as described for Acid Preparation 8, 285 mg, 1.27 mmol) in dioxane (1.3 mL) was added hexacarbonylmolybdenum (264 mg, 1.0 mmol), Herrmann's catalyst (93 mg, 0.1 mmol)and a solution of Na2CO3 in water (636 mg in 2 mL water). The suspension was heated in a microwave at 165 0C for 15 minutes (high absorption). The vial was vented, acidified with 1 N HCI (to pH 2). The reaction mixture was filtered through diatomaceous earth, washed with EtOAc and the organic layer was washed with saturated aqueous NaCI (3x). The organic extract was concentrated to yield the title compound as a pink solid (65 mg, 17%).

References:

WO2008/65508,2008,A1 Location in patent:Page/Page column 31-32