[ CAS No. 152626-78-3 ]

Name: 152626-78-3|5-Bromo-6-methoxy-1H-indazole|97%
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Product Details of [ 152626-78-3 ]

CAS No. :	152626-78-3	MDL No. :	MFCD11007880
Formula :	C₈H₇BrN₂O	Boiling Point :	363.4°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	227.06 g/mol	Pubchem ID :	15278593
Synonyms :

Safety of [ 152626-78-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 152626-78-3 ]

Upstream synthesis route of [ 152626-78-3 ]
Downstream synthetic route of [ 152626-78-3 ]

[ 152626-78-3 ] Synthesis Path-Upstream 1~3

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Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: With hydroxylamine hydrochloride; potassium carbonate In 1,2-dimethoxyethane at 100℃; for 1 h; Stage #2: With hydrazine hydrate In 1,2-dimethoxyethane; ISOPROPYLAMIDE at 150℃;	Step 25-bromo-6-methoxy-1H-indazole (Compound A33)Compound (9 g, 38.6 mmol), o-hydroxylamine hydrochloride (3.23 g, 38.6 mmol), and potassium carbonate (5.87 g, 42.5 mmol) were dissolved in 1,2-dimethoxyethane (90 mL), and the mixture was stirred at 100°C for 1 hour. After cooling to room temperature, the solid substance was filtered off, and the filtrate was evaporated off under reduced pressure. Dimethyl acetamide (90 mL) and hydrazine monohydrate (18 mL) were added thereto, and the mixture was stirred at 150°C overnight. After cooling to room temperature, water was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then the solvent was evaporated off under reduced pressure to give Compound A33 (8.26 g, yield: 94percent) as a yellow paste. ESI-MS m/z: 227, 229 [M+H]⁺; ¹H-NMR (300 MHz, CDCl₃) δ(ppm): 3.96 (s, 3H), 6.92 (s, 1H), 7.94 (d, J = 1.1 Hz, 2H).

Reference： [1] Patent: EP2308880, 2011, A1, . Location in patent: Page/Page column 47

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Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5129 - 5140

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[ 331-64-6 ]
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Reference： [1] Patent: EP2308880, 2011, A1,

[ 152626-78-3 ] Synthesis Path-Downstream 1~26

Yield	Reaction Conditions	Operation in experiment
		a mixture of iron powder (2.4 g, 43 mmol), 9 mL of ethanol, 7 mL of water and 0.2 mL of conc. hydrochloric acid was heated to 80 C. and the previously prepared nitro compound (2 g, 8.1 mmol) was added portionwise to just maintain reflux after the heat source was removed. After the rapid reflux had subsided, the mixture was allowed to cool to about 70 C. and was filtered through Celite which was then washed with methylene chloride. The aqueous layer was separated and washed with methylene chloride and the combined organic layers were dried, filtered and evaporated in vacuo to give 1.55 g of brown solid. This was purified by flash chromatography on silica gel (methylene chloride) to give 1.18 g (67% yield) of the aniline as a white solid. Preparation of 5-bromo-6-methoxy-1H-indazole:

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Reference： [1]Patent: EP2308880,2011,A1

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Yield	Reaction Conditions	Operation in experiment
94%		Step 25-bromo-6-methoxy-1H-indazole (Compound A33)Compound (9 g, 38.6 mmol), o-hydroxylamine hydrochloride (3.23 g, 38.6 mmol), and potassium carbonate (5.87 g, 42.5 mmol) were dissolved in 1,2-dimethoxyethane (90 mL), and the mixture was stirred at 100C for 1 hour. After cooling to room temperature, the solid substance was filtered off, and the filtrate was evaporated off under reduced pressure. Dimethyl acetamide (90 mL) and hydrazine monohydrate (18 mL) were added thereto, and the mixture was stirred at 150C overnight. After cooling to room temperature, water was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then the solvent was evaporated off under reduced pressure to give Compound A33 (8.26 g, yield: 94%) as a yellow paste. ESI-MS m/z: 227, 229 [M+H]+; 1H-NMR (300 MHz, CDCl3) delta(ppm): 3.96 (s, 3H), 6.92 (s, 1H), 7.94 (d, J = 1.1 Hz, 2H).

Reference： [1]Patent: EP2308880,2011,A1 .Location in patent: Page/Page column 47

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