ChemicalBook CAS DataBase List 1H-Indazole-3-acetic acid, Methyl ester

1H-Indazole-3-acetic acid, Methyl ester synthesis

5synthesis methods

Product Name:1H-Indazole-3-acetic acid, Methyl ester
CAS Number:131666-74-5
Molecular formula:C10H10N2O2
Molecular Weight:190.2

67-56-1

26663-42-3

131666-74-5

Concentrated sulfuric acid (0.543 g, 5.53 mmol) was slowly added to a stirred solution of indazole-3-acetic acid (4.86 g, 27.5 mmol) in methanol (250 mL). The reaction mixture was refluxed at 68 °C for 16 h, during which the reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the methanol was evaporated to dryness by rotary evaporator. The residual gel was alkalized to pH 7-8 with saturated sodium bicarbonate solution and subsequently extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated by rotary evaporator under reduced pressure to give methyl 2-(1H-indazol-3-yl)acetate (4.90 g, 25.7 mmol, 93% yield) as a light brown solid.

67-56-1 Synthesis

67-56-1
789 suppliers
$9.00/25ml

26663-42-3 Synthesis

26663-42-3
86 suppliers
$73.00/100mg

131666-74-5
45 suppliers
$63.00/100mg

Yield:131666-74-5 93%

Reaction Conditions:

with sulfuric acid at 68; for 16 h;

Steps:

Synthesis of (1H-Indazol-3-yl)-acetic acid methyl ester (35-2):

To a stirred solution of 2-(1H-indazol-3-yl)acetic acid (35-1) (4.86 g, 27.5 mmol) in Methanol (250 mL ) was added sulfuric acid (0.543 g, 5.53 mmol) and the reaction was refluxed at 68°C for 16 h. Reaction progress was monitored by TLC. The MeOH was evaporated to dryness and the residual gum was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and evaporated in vacuo to yield methyl 2-(1H-indazol-3-yl)acetate (35-2) (4.90 g, 25.7 mmol, 93 %) as a light brown solid.

References:

WO2017/197046,2017,A1 Location in patent:Page/Page column 328

26663-42-3 Synthesis

26663-42-3
86 suppliers
$73.00/100mg

131666-74-5
45 suppliers
$63.00/100mg

References

26663-42-3 Synthesis

26663-42-3
86 suppliers
$73.00/100mg