5-Bromo-1H-pyrazole[3,4-b]pyridin-3-amine

5-Bromo-1H-pyrazole[3,4-b]pyridin-3-amine - Names and Identifiers

Name	5-Bromo-1H-pyrazolo[3,4-b]pyridin-3-amine
Synonyms	3-Amino-5-bromo-1H-pyrazo... 5-Bromo-1H-pyrazole[3,4-b]pyridin-3-amine 5-Bromo-1H-pyrazolo[3,4-b]pyridin-ylamine 5-Bromo-1H-pyrazolo[3,4-b]pyridin-3-amine 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-amine 3-Amino-5-bromo-1H-pyrazolo[3,4-B]pyridine 1H-Pyrazolo[3,4-b]pyridin-3-aMine,5-broMo- 1H-pyrazolo[3,4-b]pyridin-3-amine, 5-bromo- 5-BROMO-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE 5-Bromo-1H-pyrazolo[3,4-b]pyridin-3-amine, 3-Amino-7-aza-5-bromo-1H-indazole
CAS	405224-24-0
InChI	InChI=1/C6H5BrN4/c7-3-1-4-5(8)10-11-6(4)9-2-3/h1-2H,(H3,8,9,10,11)

5-Bromo-1H-pyrazole[3,4-b]pyridin-3-amine - Physico-chemical Properties

Molecular Formula	C6H5BrN4
Molar Mass	213.03
Density	1.994
Boling Point	429.1±40.0 °C(Predicted)
Flash Point	213.334°C
Vapor Presure	0mmHg at 25°C
pKa	9.55±0.40(Predicted)
Storage Condition	2-8°C(protect from light)
Refractive Index	1.824

5-Bromo-1H-pyrazole[3,4-b]pyridin-3-amine - Risk and Safety

Hazard Symbols	Xn - Harmful
Risk Codes	22 - Harmful if swallowed

5-Bromo-1H-pyrazole[3,4-b]pyridin-3-amine - Reference Information

Use

3-amino-5-bromo-1H-pyrazolo [3,4-B] pyridine is an organic intermediate.

Preparation

3-amino-5-bromo-1H-pyrazolo [3,4-B] pyridine can be used as a raw material to prepare 2-methoxy-nicotinonitrile first, and then bromate to obtain 2-methoxy-nicotinonitrile, finally, the ring was closed to obtain 3-amino-5-bromo-1H-pyrazolo [3,4-B] pyridine. Step 1: 4.98g(217mmol) of sodium was added to 80ml of anhydrous methanol by 2-methoxy-nicotinil. The reaction medium was stirred at room temperature for 10 minutes, and then 10g(72.2mmol) of 2-chloronicotinonitrile was added at 0 ℃. The reaction medium was stirred at 25 ℃ for 16 hours. The reaction was hydrolyzed by slowly adding water at 0°C. After returning to room temperature, the resulting precipitate was filtered, rinsed with water, and then dried at 50°C to obtain 7.85g(81%) 2-methoxy-nicotinil in yellow solid form. Step 2:5-bromo-2-methoxy-nicotinil 12.23g(149mmol) of sodium acetate and then 7.66ml(149mmol) of bromine were added to a 29ml acetic acid solution of 10g (74.6mmol) 2-methoxy-nicotinil at 0°C. The reaction mixture was heated overnight at 70°C. After returning to room temperature, the reaction medium was added to an ice bath, the resulting precipitate was filtered, rinsed with water, and then dried at 50°C to obtain 11.6g(73%) 5-bromo-2-methoxy-nicotinil in white solid form. Step 3: 35ml(23.47mmol) of hydrazine was added to 5g(23.47mmol) of 5-bromo-2-methoxynicotinil at room temperature. The reaction medium was kept at 100 ℃ for 3 hours. After returning to room temperature, the resulting precipitate was filtered, rinsed with water, and then dried at 50°C to obtain 3.6g(72%) 3-amino-5-bromo-1H-pyrazolo [3,4-B] pyridine in yellow solid form.

Last Update：2024-04-09 02:00:08