ChemicalBook CAS DataBase List Methyl 1H-indazole-6-carboxylate

Methyl 1H-indazole-6-carboxylate synthesis

14synthesis methods

Product Name:Methyl 1H-indazole-6-carboxylate
CAS Number:170487-40-8
Molecular formula:C9H8N2O2
Molecular Weight:176.17

18595-18-1

170487-40-8

Example 1 Preparation of 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(dimethylcarbamoyl)-1H-indazol-3-yl)cyclohex-3-enecarboxylic acid (1A) Step 1: Preparation of methyl 1H-indazole-6-carboxylate (A-2). Methyl 3-amino-4-methylbenzoate (A-1) (5.0 g, 30.2 mmol) was dissolved in acetic acid (140 mL). An aqueous solution of sodium nitrite (2.1 g, 30.2 mmol) was added slowly and dropwise (3.5 mL) to the reaction mixture under cooling in an ice bath. After removing the ice bath, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, about half of the solvent was removed by evaporation, and the remaining mixture was diluted with water (80 mL) and extracted with ethyl acetate (3 x 30 mL). The organic phases were combined, washed sequentially with water and saturated saline (2×200 mL each), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the product A-2 (4.4 g, 83% yield). LCMS (ESI): calculated value for C9H8N2O2, [M + H]+: 177, measured value: 177.

18595-18-1 Synthesis

18595-18-1
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$8.00/10g

170487-40-8
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$6.00/250mg

Yield:170487-40-8 83%

Reaction Conditions:

with acetic acid;sodium nitrite in water at 20; for 5 h;Acidic aqueous solution;

Steps:

1
To a mixture of 3-amino-4-methyl-benzoic acid methyl ester (15g, 90.9 mmol) in HOAc (400 mL) was added a solution OfNaNO₂ (6.27g, 90.9 mmol) in H₂O (9OmL) dropwise. The mixture was stirred at ambient temperature for five hr. then concentrated in vacuo. The resulting solid was triturated with ethyl acetate (400 mL) and filtered. The filtrate was concentrated to afford the title compound (13.3g, 83%). m/z (M+H) = 177.18

References:

FOREST LABORATORIES HOLDINGS LIMITED WO2008/61109, 2008, A2 Location in patent:Page/Page column 29-30

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704-91-6 Synthesis