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Chemical Structure| 189089-90-5
Chemical Structure| 189089-90-5
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Product Details of [ 189089-90-5 ]

CAS No. :189089-90-5 MDL No. :MFCD02083337
Formula : C14H10N2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :DUNCEEUEBVPMEV-UHFFFAOYSA-N
M.W : 302.31 Pubchem ID :24103658
Synonyms :

Safety of [ 189089-90-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 189089-90-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 189089-90-5 ]
  • Downstream synthetic route of [ 189089-90-5 ]

[ 189089-90-5 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 124-38-9 ]
  • [ 143141-23-5 ]
  • [ 189089-90-5 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -35℃;
Stage #2: at -55 - 20℃; for 16 h;
4.2.23
1-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (17)
In a heat dried and nitrogen purged tricol round bottom flask, 5 (1.05 g, 4.07 mmol) was solubilized in dry THF (15 mL), cooled to -35 °C then lithium diisopropylamide (5.1 mL, 10.16 mmol, 2 M) was added slowly.
The mixture was then cooled to -55 °C and dry ice was added slowly.
The mixture was left to warm up to room temperature under stirring overnight.
The reaction was quenched with water and extracted with EtOAC.
The aqueous layer was acidified by the addition of a 6 N hydrochloric acid solution to pH = 1 and extracted with EtOAC.
The latter organic layer was washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 1.09 g of the expected product as a beige solid in 88percent yield. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 13.87 (br, 1H), 8.51 (dd, J = 1.6, 4.7 Hz, 1H), 8.26 (d, J = 7.0 Hz, 2H), 8.13 (dd, J = 1.6, 7.9 Hz, 1H), 7.77 (dd, J = 7.2 Hz, 1H), 7.72-7.65 (m, 2H), 7.39 (dd, J = 4.7, 7.9 Hz, 1H), 7.28 (s, 1H).
13C NMR (75 MHz, DMSO-d6) δ (ppm): 164.4, 149.5, 147.3, 138.5, 135.1, 133.3, 132.1, 129.8 (2C), 128.3 (2C), 121.1, 120.7, 112.5.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1019 - 1022
[3] Tetrahedron, 1997, vol. 53, # 10, p. 3637 - 3648
  • 2
  • [ 271-63-6 ]
  • [ 189089-90-5 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 10, p. 3637 - 3648
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1019 - 1022
[3] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
  • 3
  • [ 189089-91-6 ]
  • [ 189089-90-5 ]
Reference: [1] Patent: WO2006/50976, 2006, A1, . Location in patent: Page/Page column 30
  • 4
  • [ 98-09-9 ]
  • [ 189089-90-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1019 - 1022
[2] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
  • 5
  • [ 189089-90-5 ]
  • [ 136818-50-3 ]
Reference: [1] Synlett, 2010, # 10, p. 1481 - 1484
  • 6
  • [ 64-17-5 ]
  • [ 189089-90-5 ]
  • [ 221675-35-0 ]
YieldReaction ConditionsOperation in experiment
94% for 20 h; Reflux 4.2.24
Ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (18)
Compound 17 (302 mg, 1.00 mmol), EtOH (20 mL) and concentrated sulfuric acid (0.2 mL) were mixed in a round bottom flask and stirred under reflux for 20 h.
The reaction mixture was cooled to room temperature and concentrated under reduced pressure.
The residue was solubilized in EtOAc and washed three times with a saturated sodium hydrogenocarbonate solution, washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure.
The crude product was purified by chromatography on silica gel column, CH2Cl2/EtOAc 8:2, to give 178 mg of the expected product as a white solid in 94percent yield. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 12.49 (br, 1H), 8.41 (dd, J = 1.7, 4.6 Hz, 1H), 8.11 (dd, J = 1.6, 8.0 Hz, 1H), 7.17 (s, 1H), 7.16 (dd, J = 4.6, 8.0 Hz, 1H), 3.34 (q, J = 7.1 Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H).
13C NMR (75 MHz, DMSO-d6) δ (ppm): 161.5, 149.3, 147.2, 131.2, 128.3, 119.5, 117.3, 106.9, 61.1, 14.7.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1019 - 1022
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