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[ CAS No. 17288-35-6 ]

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2D
Chemical Structure| 17288-35-6
Chemical Structure| 17288-35-6
Structure of 17288-35-6 *Storage: {[proInfo.prStorage]}

Quality Control of [ 17288-35-6 ]

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Related Doc. of [ 17288-35-6 ]

SDS

Product Details of [ 17288-35-6 ]

CAS No. :17288-35-6MDL No. :MFCD09955613
Formula : C8H6N2O2 Boiling Point : 446.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :162.15Pubchem ID :22612670
Synonyms :

Computed Properties of [ 17288-35-6 ]

TPSA : 66 H-Bond Acceptor Count : 3
XLogP3 : 0.9 H-Bond Donor Count : 2
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 17288-35-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17288-35-6 ]

  • Upstream synthesis route of [ 17288-35-6 ]
  • Downstream synthetic route of [ 17288-35-6 ]

[ 17288-35-6 ] Synthesis Path-Upstream   1~14

  • 1
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YieldReaction ConditionsOperation in experiment
82%
Stage #1: With lithium hydroxide In ethanol; water for 16.00 h;
Stage #2: Acidic conditions
3-Amino-2-chloro-pyridine 4f (150 mg, 1.17 mmol), ethyl pyruvate 8 (0.25 ml, 2.00 mmol), pyridinium p-toluenesulfonate, (73 mg, 0.29 mmol) and tetraethoxy-silane (0.26 ml, 1.18 mmol) were suspended in 0.4 ml pyridine and stirred for 24 h at 20 °C. Afterwards Pd[P(C6H6)3]4 (70 mg, 0.06 mmol) and N,N-dicyclohexylmethylamine (0.35 ml, 2.06 mmol) were added and the reaction mixture was heated in a microwave oven to 160 °C for 20 min. The reaction mixture is diluted with 100 ml dichloromethan and extracted two times with 50 ml of a half saturated aqueous sodium hydrogencarbonat solution. The organic layer was dried with sodium sulfate, the solvent was evaporated under reduced pressure and the crude product was purified using chromatography method P3, yielding 190 mg (1.00 mmol) of 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester. The ester was dissolved in 17 ml ethanol and 5 ml water. To this solution lithium hydroxide (120 mg, 5.00 mmol) was added. After 16 h the pH value of the reaction mixture was adjusted to pH 4 and the solvent is evaporated in vacuum. The crude product was purified using an acid ion exchanger (Strata-X-C, Phenomenex), yielding of 155 mg (82percent) of the title compound. Purity by method A1: >95percent; MS (ESI) m/z 163 (M + H)+; 1H NMR (DMSO) δ (ppm) 13.34 (br, 1H), 8.77 (d, J = 5.3 Hz, 1H), 8.53 (d, J = 8.3 Hz, 1H), 7.73 (dd, J = 5.4 Hz, J = 8.3 Hz, 1H), 7.33 (br, 1H); 13C NMR (500 MHz, DMSO) δ (ppm) 161.4 (s), 138.0 (s), 136.1 (s), 135.8 (s), 132.7 (s), 128.6 (s), 119.6 (s), 101.2 (s).
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 660 - 668
[2] Patent: WO2004/104001, 2004, A2. Location in patent: Page 42-43
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Reference: [1] Patent: EP1479680, 2004, A1. Location in patent: Page 48
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Patent: WO2004/104001, 2004, A2
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Patent: WO2004/104001, 2004, A2
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Reference: [1] Patent: WO2004/104001, 2004, A2
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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  • [ 5470-18-8 ]
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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  • [ 23596-34-1 ]
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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  • [ 64362-41-0 ]
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
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Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 660 - 668
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