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[ CAS No. 153034-90-3 ]

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Chemical Structure| 153034-90-3
Chemical Structure| 153034-90-3
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Product Details of [ 153034-90-3 ]

CAS No. :153034-90-3 MDL No. :MFCD03095294
Formula : C6H3ClINO Boiling Point : 326.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :267.45 g/mol Pubchem ID :10038637
Synonyms :

Safety of [ 153034-90-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153034-90-3 ]

  • Upstream synthesis route of [ 153034-90-3 ]
  • Downstream synthetic route of [ 153034-90-3 ]

[ 153034-90-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 78607-36-0 ]
  • [ 109-94-4 ]
  • [ 153034-90-3 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3 h;
Stage #2: at -78℃; for 1.5 h;
Example 1 :N-(2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamideStep 1 :2-Chloro-4-iodonicotinaldehydeA mixture of 2-chloro-3-iodopyridine (5.0 g, 21 mmol) in dry THF (30 mL) was slowly added to a cold (-78 °C) solution of lithium diisopropylamide (15 mL, 30 mmol) in dry THF (50 mL). The resulting mixture was stirred for 3 h at this temperature. Ethyl formate (4.0 g, 54 mmol) was then added. Stirring was continued for 1.5 h at the same temperature. Water (10 mL) was added to quench the reaction, and then the resulting mixture was warmed to room temperature. 2M HC1 (50 mL) was added and then the THF was removed under reduced pressure. The aqueous residue was extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified on silica gel (diethyl ether: petroleum ether = 1 : 4) to give the desired product 2-chloro- 4-iodonicotinaldehyde as a yellow solid (3.0 g, 54percent yield). NMR (500 MHz, CDC13): δ 10.22 (s, 1H), 8.09 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H).
Reference: [1] Synthetic Communications, 1996, vol. 26, # 23, p. 4421 - 4436
[2] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7832 - 7838
[3] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 5, p. 1039 - 1044
[4] Patent: WO2012/66061, 2012, A1, . Location in patent: Page/Page column 76-77
  • 2
  • [ 153034-86-7 ]
  • [ 109-94-4 ]
  • [ 153034-90-3 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3 h;
Stage #2: at -78℃; for 1.5 h;
A mixture of 2-chloro-3-iodopyridine(5.0g, 21mmol) in dry THF (30 mL) was slowly added to a cold (-78°C) solution oflithiumdiisopropylamide(15 mL, 30mmol) in dry THF (50 mL). The resulting mixture was stirred for 3h at this temperature.Ethylformate(4.0g, 54mmol) wasthenadded.Stirring continued for 1.5 h at the same temperature.Water (10 mL) was added to quench the reaction, and then theresultingmixture was warmed toroom temperature.2 MHCl(50 mL) was added and then the THF was removed under reduced pressure.The aqueous residue was extracted withethyl acetate(2 x 50 mL).The combined organic extracts were washed with brine, dried over Na2SO4andconcentrated under reduced pressure.The residuewas purified on silica gel(diethyl ether/petroleum ether1:4)to give the desired product as a yellow solid(3.0 g, 54percent yield).HNMR(500 MHz, CDCl3):δ10.22(s, 1H), 8.09(d, J =5.0Hz, 1H), 7.95(d,J =5.0Hz, 1H).
52%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3 h; Inert atmosphere; Schlenk technique
Stage #2: at -78℃; for 1.5 h; Inert atmosphere; Schlenk technique
According to the literature,17 a dry, argon-flushed Schlenk flask equipped with a magnetic stirring bar and a septum was charged with a solution of LDA (18.0 mmol, 1.0 M in THF) and cooled to –78 °C. 2-Chloro-3-iodopyridine (3.1 g, 13.0 mmol) was added dropwise tothe cooled solution. The resulting mixture was stirred for 3 h at –78 °C. Ethyl formate (2.5 g, 34.0 mmol) was then added and stirred for 1.5 hat –78 °C. The resulting solution was quenched with sat. aq NH4Cl (80 mL), extracted with EtOAc (3 × 120 mL), and the combined organic phases were dried (anhyd MgSO4). After filtration, the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography on silica gel (i-hexane/EtOAc, 9:1 to 8:2 +Et3N 2percent) yielding 2-chloro-4-iodonicotinaldehyde as a yellow solid(1.8 g, 52percent). 1H NMR (400 MHz, CDCl3): δ = 10.19 (s, 1 H), 8.07 (d, J = 5.1 Hz, 1 H),7.94 (d, J = 5.1 Hz, 1 H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4370 - 4376
[2] Synthesis (Germany), 2018, vol. 50, # 1, p. 155 - 169
[3] Organic Letters, 2018, vol. 20, # 2, p. 345 - 348
  • 3
  • [ 153034-90-3 ]
  • [ 688357-19-9 ]
Reference: [1] Patent: WO2013/9582, 2013, A1,
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5800 - 5816
  • 4
  • [ 153034-90-3 ]
  • [ 871836-51-0 ]
YieldReaction ConditionsOperation in experiment
70% With hydrazine hydrate In ethanol at 0 - 20℃; To a solution of 2-chloro-4-iodonicotinaldehyde (101) (1.33 g, 5 mmol) in EtOH (10 mL), N2H4H2O (480 uL, 2 eq, 10 mmol) was added slowly at 0 - 5 °C.
The solution was stirred at 10 °C for 1 h.
Then additional amount of N2H4H2O (480 uL, 2 eq, 10 mmol) was added slowly and the resulting mixture was stirred at RT overnight.
The mixture was concentrated in vacuo, brine (20 mL) was added and then extracted with ethyl acetate (3 * 50 mL).
The combined organic layer was washed with brine (20 mL), dried over MgSO4 and filtered.
The filtrate was concentrated in vacuo to afford the crude product.
19% With hydrazine In ethanol at 20℃; for 15 h; Step 2:4-Chloro-lH-pyrazolo[4,3-c]pyridine To a mixture of 2-chloro-4-iodonicotinaldehyde (1.0 g, 3.7 mmol) in ethanol (6.0 mL) was added 3.0 mL of hydrazine (excess). The mixture was stirred at room temperature for 15 h and then concentrated under reduced pressure. The residue was diluted with water (30 mL) and extracted with dichloromethane (300 mL). The organic extract was washed with brine, dried over Na2S04, and concentrated under reduced pressure. The residue was dissolved in dichloromethane (5 mL) and stirred for 5 min. The precipitated solid was isolated by filtration and dried to give the desired intermediate 4-chloro-lH-pyrazolo[4,3-c]pyridine as a grey solid (110 mg, 19percent yield), which was used in the next step without further purification. LCMS(ESI) m/z: 154.1 [M+H+]
Reference: [1] Patent: EP2252293, 2018, B1, . Location in patent: Paragraph 0257; 0258
[2] Patent: WO2012/66061, 2012, A1, . Location in patent: Page/Page column 77
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4370 - 4376
  • 5
  • [ 153034-90-3 ]
  • [ 1186647-69-7 ]
Reference: [1] Patent: EP2252293, 2018, B1,
  • 6
  • [ 153034-90-3 ]
  • [ 1171919-75-7 ]
Reference: [1] Patent: US2010/298334, 2010, A1, . Location in patent: Page/Page column 97
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