Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate
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Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate
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CAS No:
105486-72-4
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Formula:
C7H9BrN2O2
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Chemical Name:
Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate
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Synonyms:
ETHYL 5-BROMO-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE;5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester;1H-Pyrazole-4-carboxylic acid, 5-bromo-1-methyl-, ethyl ester;ETHYL 5-BROMO-1-METHYLPYRAZOLE-4-CARBOXYLATE;SCHEMBL2315523;CTK8C2961;DTXSID70693302;ACN-P000045;KS-00000OT3;1249AA
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CAS No:
Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate Basic Attributes
233.064
231.98500
DTXSID70693302
2933199090
Characteristics
44.1
1.5
1.58±0.1 g/cm3(Predicted)
290.7±20.0 °C(Predicted)
129.621ºC
1.578
0.002mmHg at 25°C
Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate Use and Manufacturing
Intermediate 1: (5-Bromo-1-methyl-1H-pyrazol-4-yl)-(octahydro-quinolin-1-yl)methanone; Step 1. ; 5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester; To a mixture of t-butyl nitrite (29.5 mL, 221.5 mmol), cupric bromide (39.7 g, 177.5 mmol), and acetonitrile was added 5-amino-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (25 g, 148 mmol) in portions over 30 minutes. The reaction mixture was stirred at ambient temperature for 2 h, then at 65° C. for 1 h. The mixture was then poured into 6N HCl (400 mL) and extracted with dichloromethane. After concentration in vacuo, the crude residue was purified by flash chromatography with a gradient of 0-20percent ethyl acetate/hexanes to give 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (28 g, 81percent).5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (5.0 g, 29.6 mmol) was added portionwise to a mixture of tert-butyl nitrite (4.57 g, 44.3 mmol) and copper (II) bromide (7.92 g, 35.5 mmol) in acetonitrile (20 mL). The mixture was heated to 60°C for 2 h. The resulting mixture was poured into 6M HCl (200 mL) and extracted with dichloromethane (3 x 250 mL). The combined organics was dried on magnesium sulfate and concentrated in vacuo. The crude material was purified by column chromatography (SiOStep 1.[0506] to a solution of compound 32b (5.6 g, 25.57 mmol) in DMF(200 ml) was added mel (14.52 g, 102.28 mmol, 6.37 ml) andCs2CO3 (33.32 g, 102.28 mmol). The mixture was stirred at 25 °C for 12 hrs. The mixture was diluted with H2O (1000 ml) and extracted with ethyl acetate (500 ml), then the organic layer was washed with brine (500 ml x 3), dried over Na2SO4 and concentrated. The residue (4 g) was purified by preparatory-hplc (basic condition). The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate=10/l to 5: 1). Compound 32c (1g, yield: 16.8percent) was obtained as a white solid. Compound 32d (2 g, yield: 33.6percent) was obtained as a white solid.
Computed Properties
Molecular Weight:233.06
XLogP3:1.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:231.98474
Monoisotopic Mass:231.98474
Topological Polar Surface Area:44.1
Heavy Atom Count:12
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate
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