ChemicalBook CAS DataBase List 6-BROMO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER

6-BROMO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER synthesis

9synthesis methods

Product Name:6-BROMO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER
CAS Number:885518-49-0
Molecular formula:C9H7BrN2O2
Molecular Weight:255.07

Methyl 1-Acetyl-6-broMo-1H-indazole-4-carboxylate

1346597-55-4

6-BROMO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER

885518-49-0

Step 6: Synthesis of methyl 6-bromo-1H-indazole-4-carboxylate To a stirred solution of methyl 1-acetyl-6-bromo-1H-indazole-4-carboxylate (18 g, 61.0 mmol) in methanol (350 mL) was slowly added 6N HCl (350 mL). The reaction mixture was stirred at 60 °C for 8 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Subsequently, the reaction mixture was alkalized with saturated NaHCO3 solution to pH 8. The precipitated solid was collected by filtration and dried under vacuum. The dried solid was stirred in ether for 15 min, filtered again and dried to give methyl 6-bromo-1H-indazole-4-carboxylate (11 g, 71.7% yield).

1346597-55-4 Synthesis

1346597-55-4
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885518-49-0
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$6.00/250mg

Yield: 71.7%

Reaction Conditions:

Stage #1:methyl 1-acetyl-6-bromo-1H-indazole-4-carboxylate with hydrogenchloride in methanol;water at 60; for 8 h;
Stage #2: with sodium hydrogencarbonate in methanol;water; pH=8

Steps:

[01044] Step 6: methyl 6-bromo-lH-indazole-4-carboxylate[01045] To a stirred solution of methyl l-acetyl-6-bromo-lH-indazole-4-carboxylate (18 g, 61.0 mmol) in methanol (350 mL), 6N HC1 (350 mL) was added and stirred it at 60 °C for 8 h. On completion of reaction, solvent was removed under reduced pressure then basified with saturated NaHC0₃ solution till pH 8. The solid precipitate was filtered and dried under vacuum before being stirred in diethyl ether for 15 min, filtered and dried to afford methyl 6-bromo-lH-indazole-4-carboxylate (11 g, 71 .7%).

References:

EPIZYME, INC.;KUNTZ, Kevin, Wayne;OLHAVA, Edward, James;CHESWORTH, Richard;DUNCAN, Kenneth, William WO2012/118812, 2012, A2 Location in patent:Page/Page column 313

1000342-11-9 Synthesis