ChemicalBook CAS DataBase List Methyl 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

Methyl 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylate synthesis

3synthesis methods

Product Name:Methyl 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylate
CAS Number:916326-80-2
Molecular formula:C9H8BrN3O2
Molecular Weight:270.08

74-88-4
340 suppliers
$15.00/10g

Methyl 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

916326-80-2
25 suppliers
$297.00/100mg

Yield:916326-80-2 97%

Reaction Conditions:

Stage #1: methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylatewith sodium hydride in tetrahydrofuran at 0; for 0.25 h;
Stage #2: methyl iodide in tetrahydrofuran at 0 - 20;

Steps:

11

Sodium hydride (47 mg, 60% in mineral oil, 1.18 mmol) was added in portions to a solution of 5-bromo-lΗ-pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester Compound Ib (0.3 g, 1.17 mmol) in dry THF (20 mL) at 0⁰C. The mixture was stirred at 0 ⁰C for 15 minutes then methyl iodide (80 μl, 1.29 mmol) was added. The reaction was warmed to room temperature gradually and stirred overnight, the solvent was removed and the residue was purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-l-methyl-lH-pyrazolo[3,4-b]pyridine-3- carboxylic acid methyl ester Compound 11a (0.31 g, 97% yield) as a white powder. ¹H NMR (400 MHz, CDCl₃) δ 9.89 (s, i), 4.51 (s, 3H), 3.37 (s, 3H); MS (ESI) m/z: 271 (M+H⁺).

References:

WO2006/130673,2006,A1 Location in patent:Page/Page column 102

ethyl 5-chloro-[1,2,4]triazolo[4,3-a]pyrimidine-7-carboxylat

916325-84-3
62 suppliers
$100.00/100mg

74-88-4
340 suppliers
$15.00/10g

916326-80-2
25 suppliers
$297.00/100mg

References

Methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate

916325-83-2
64 suppliers
$63.00/100mg

916326-80-2
25 suppliers
$297.00/100mg

References