ChemicalBook CAS DataBase List METHYL 5-BROMO-1H-INDAZOLE-3-CARBOXYLATE

METHYL 5-BROMO-1H-INDAZOLE-3-CARBOXYLATE synthesis

5synthesis methods

Product Name:METHYL 5-BROMO-1H-INDAZOLE-3-CARBOXYLATE
CAS Number:78155-74-5
Molecular formula:C9H7BrN2O2
Molecular Weight:255.07

1077-94-7

67-56-1

METHYL 5-BROMO-1H-INDAZOLE-3-CARBOXYLATE

78155-74-5

Step 2: Concentrated sulfuric acid (1 mL) was slowly added to a suspension of 5-bromo-1H-indazole-3-carboxylic acid (1.30 g, 5.39 mmol) in anhydrous methanol (50 mL) under argon protection. The reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, the solution was cooled to room temperature and subsequently evaporated under reduced pressure to remove methanol. The residue was dissolved in ethyl acetate and washed with deionized water. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to afford methyl 5-bromo-1H-indazole-3-carboxylate (1.35 g, 5.29 mmol, 98% yield) as a white solid. The product was confirmed by 1H NMR (DMSO-d6): δ 14.13 (s, 1H), 8.21 (d, J = 1.6 Hz, 1H), 7.67 (d, J = 7.2 Hz, 1H), 7.59 (dd, J = 7.2, 1.2 Hz, 1H), 3.92 (s, 3H); ESIMS analysis result: C9H7BrN2O2 m/z 256.0 (M + H).

1077-94-7 Synthesis

1077-94-7
186 suppliers
$11.00/250mg

67-56-1 Synthesis

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

78155-74-5
116 suppliers
$9.00/100mg

Yield:78155-74-5 98%

Reaction Conditions:

with sulfuric acid for 4 h;Reflux;Inert atmosphere;

Steps:

25.2 Step 2

Concentrated sulfuric acid (1 mL) was added to a suspension of 5- bromo-lH-indazole-3-carboxylic acid (CXV) (1.30 g, 5.39 mmol) in dry MeOH (50 mL) and heated to reflux for 4 h under argon. The solution was cooled to room temperature and the MeOH was evaporated under vacuum. The residue was dissolved in EtOAc and washed with water. The organic phase was dried over Na₂S0₄, filtered and concentrated to afford methyl 5-bromo-lH-indazole-3-carboxylate (CXVI) as a white solid (1.35 g, 5.29 mmol, 98% yield). 1H NMR (DMSO-d₆) δ ppm 14.13 (s, 1H), 8.21 (d, J = 1.6 Hz, 1H), 7.67 (d, J= 7.2 Hz, 1H), 7.59 (dd, J= 7.2, 1.2 Hz, 1H), 3.92 (s, 3H); ESIMS found for C₉H₇BrN₂0₂ mlz 256.0 (M+H).

References:

WO2013/40215,2013,A1 Location in patent:Paragraph 00340

43120-28-1 Synthesis