Methyl 1H-indazole-6-carboxylate Chemical Properties

Melting point:

142-144℃

Boiling point:

345.2±15.0 °C(Predicted)

Density 

1.324±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

12.43±0.40(Predicted)

color 

White to Light yellow to Light orange

Water Solubility 

Soluble in water.

InChI

InChI=1S/C9H8N2O2/c1-13-9(12)6-2-3-7-5-10-11-8(7)4-6/h2-5H,1H3,(H,10,11)

InChIKey

TUSICEWIXLMXEY-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(C(OC)=O)=C2)C=N1

Safety Information

WGK Germany 

3

HS Code 

2933998090

Methyl 1H-indazole-6-carboxylate Usage And Synthesis

Uses

Methyl 1H-indazole-6-carboxylate?is used in organic synthesis.

Synthesis

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.

References

[1] Patent: WO2008/61109, 2008, A2. Location in patent: Page/Page column 29-30
[2] Patent: WO2014/26328, 2014, A1. Location in patent: Page/Page column 39-40
[3] Patent: WO2014/28597, 2014, A2. Location in patent: Page/Page column 56
[4] Patent: WO2014/26327, 2014, A1. Location in patent: Page/Page column 59
[5] Patent: WO2014/28600, 2014, A2. Location in patent: Page/Page column 50; 51

Methyl 1H-indazole-6-carboxylate(170487-40-8)Related Product Information

• Methyl 1H-indazole-6-carboxylate
• 5-(1H)INDAZOLE CARBOXYLIC ACID METHYL ESTER
• 1H-indazole-6-carboxylic acid
• 4-BROMO-6-METHYLCARBOXYLATE-1H-INDAZOLE-3-CARBOXYLIC ACID
• 4-AMINO-6-INDAZOLECARBOXYLIC ACID METHYL ESTER
• 3-HYDROXY-6-(1H)INDAZOLE CARBOXYLIC ACID METHYL ESTER
• 4-IODO-6-INDAZOLECARBOXYLIC ACID METHYL ESTER
• 4-METHOXY-6-(1H)INDAZOLE CARBOXYLIC ACID METHYL ESTER
• ETHYL 1H-INDAZOLE-6-CARBOXYLATE
• 4-CHLORO-6-INDAZOLECARBOXYLIC ACID METHYL ESTER
• 4-BROMO-3-HYDROXYMETHYL-1H-INDAZOLE-6-CARBOXYLIC ACID METHYL ESTER
• 3-BROMO-4-NITRO-6-INDAZOLECARBOXYLIC ACID METHYL ESTER
• 1H-Indazole-3,6-dicarboxylic acid, 6-methyl ester
• 4-METHOXY-3,6-DICARBOXYLIC ACID-(1H)INDAZOLE 6-METHYL ESTER
• 1H-INDAZOLE-6-CARBOXYLIC ACID, 4-BROMO-3-FORMYL-, METHYL ESTER
• 3-CHLORO-4-NITRO-6-INDAZOLECARBOXYLIC ACID METHYL ESTER
• 4-AMINO-3-IODO-6-INDAZOLECARBOXYLIC ACID METHYL ESTER
• 4-NITRO-6-INDAZOLECARBOXYLIC ACID METHYL ESTER