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[ CAS No. 51135-70-7 ]

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2D
Chemical Structure| 51135-70-7
Chemical Structure| 51135-70-7
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Product Details of [ 51135-70-7 ]

CAS No. :51135-70-7MDL No. :MFCD06739193
Formula : C11H12N2O2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :204.23Pubchem ID :19770961
Synonyms :

Computed Properties of [ 51135-70-7 ]

TPSA : 43.6 H-Bond Acceptor Count : 3
XLogP3 : 1.6 H-Bond Donor Count : 0
SP3 : 0.27 Rotatable Bond Count : 3

Safety of [ 51135-70-7 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H320-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51135-70-7 ]

  • Upstream synthesis route of [ 51135-70-7 ]
  • Downstream synthetic route of [ 51135-70-7 ]

[ 51135-70-7 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
77% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; A solution of ethyl 5-bromopyrazolo[1,5-ajpyridine-3-carboxylate (1.0 g, 3.73 mmol),methylboronic acid (448 mg, 7.46 mmol), Pd(dppf)C12 (545 mg, 0.746 mmol) and C52CO3(2.42 g, 7.46 mmol) was dissolved in DMF (5.0 mL), then the mixture was stirred at 100 °Cfor two hours. It was concentrated, and purified by silica gel chromatography with PE:EA=5: 1to obtain the desired compound as an orange solid (589 mg, 77percent). ESI MS m/z = 204.5[M+Hj.
Reference: [1] Patent: WO2017/15449, 2017, A1, . Location in patent: Page/Page column 342
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YieldReaction ConditionsOperation in experiment
53%
Stage #1: With mesitylenesulfonylhydroxylamine In dichloromethane at 0℃; for 2 h;
Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h;
General procedure: These were made using MSH or DNPH as detailed below, unless otherwise stated. A fresh solution of MSH23 in CH2Cl2 (1 equiv) was added to the substituted pyridine (1 equiv) in CH2Cl2 (10 mL) at 0 °C. After 2 h, the solvent was removed in vacuo. Alternatively, a solution of DNPH12 (1 equiv) and the substituted pyridine (1 equiv) in MeCN (40 mL) was heated at 40 °C for 18 h. The solvent was removed in vacuo. The method continues by taking the residue from either method in dry DMF (8 mL), and then ethyl propiolate (1 equiv) and K2CO3 (2 equiv) were added, and the suspension stirred at room temperature for 18 h. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic phases were washed three times with water then with brine, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient, unless otherwise stated) gave the pyrazolo[1,5-a]pyridine.
53%
Stage #1: With mesitylenesulfonylhydroxylamine In dichloromethane at 0℃; for 2 h;
Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h;
Step 2.1 : A fresh solution of O-(mesitylsulfonyl)hydroxylamine in CH2CI2 (6.0 ml_, 0.44 mol L"1, 2.6 mmol) [T. Eichenberger et al., HeIv. Chim. Acta 1986, 69(6), 1521] was added to 4-methylpyridine (1: X = Me) (248 mg, 2.66 mmol) in CH2CI2 (10 mL) at 0 0C. After 2 h, the solvent was removed in vacuo. The residue was taken up in dry DMF (8 mL), then ethyl propiolate (0.25 mL, 2.5 mmol) and K2CO3 (450 mg, 3.26 mmol) were added, and the suspension stirred at room temperature for 18 h. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic phases were washed three times with water then with brine, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with hexanes: EtOAc 97:3 to 95:5 to 9:1) gave ethyl 5-methyl- pyrazolo[1 ,5-a]pyridine-3-carboxyIate (4: X = Me) as a pale brown solid (175 mg, 53percent). 1H NMR δ (400 MHz, CDCI3) 8.39 (d, J 7.1 Hz, 1 H)1 8.34 (s, 1H), 7.93 (s, 1H), 6.76 (dd, J 7.1 , 1.9 Hz, 1 H), 4.38 (q, J 7.1 Hz, 2H), 2.47 (s, 3H), 1.41 (t, J 7.1 Hz, 3H). LCMS (APCI+) 205 (MH+, 100percent).
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 69 - 85
[2] Patent: WO2009/8748, 2009, A1, . Location in patent: Page/Page column 56
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Reference: [1] Patent: WO2015/86693, 2015, A1, . Location in patent: Page/Page column 52
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YieldReaction ConditionsOperation in experiment
2.73 g
Stage #1: With perchloric acid In tetrahydrofuran at 0℃; for 1.5 h;
Stage #2: at 0 - 35℃;
Stage #3: With potassium carbonate In N,N-dimethyl-formamide at 10 - 35℃;
To a solution of ethyl N-(mesitylsulfonyl)oxyacetoimidate (14.7 g) in THF (15 mL) was added 60percent perchloric acid (11.2 mL) at 0°, the mixture was stirred for 90 min, and to the reaction mixture was added ice water.
The insoluble substance was collected by filtration, washed with water, and dried under stream.
The residue was added to a solution of 4-methylpyridine (4.18 mL) in THF (80 mL) at 0° C., and the mixture was stirred overnight at room temperature.
The solvent was evaporated under reduced pressure, DMF (80 mL), ethyl propionate (5.21 mL) and potassium carbonate (11.9 g) were added thereto, and the mixture was stirred overnight at room temperature.
To the reaction mixture was added water, and the mixture was extracted with ethyl acetate.
The extract was washed with 1N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.73 g).
1H NMR (300 MHz, CDCl3) δ 1.41 (3H, t, J=7.2 Hz), 2.47 (3H, s), 4.38 (2H, q, J=6.9 Hz), 6.77 (1H, dd, J=7.0, 1.7 Hz), 7.93 (1H, s), 8.34 (1H, s), 8.39 (1H, d, J=7.2 Hz).
Reference: [1] Patent: US2015/266872, 2015, A1, . Location in patent: Paragraph 0739; 0740
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Reference: [1] Patent: WO2015/86693, 2015, A1,
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