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[ CAS No. 17288-32-3 ]

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2D
Chemical Structure| 17288-32-3
Chemical Structure| 17288-32-3
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Quality Control of [ 17288-32-3 ]

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Product Details of [ 17288-32-3 ]

CAS No. :17288-32-3MDL No. :MFCD11053752
Formula : C10H10N2O2 Boiling Point : 355.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :190.20Pubchem ID :11579250
Synonyms :

Computed Properties of [ 17288-32-3 ]

TPSA : 55 H-Bond Acceptor Count : 3
XLogP3 : 1.6 H-Bond Donor Count : 1
SP3 : 0.20 Rotatable Bond Count : 3

Safety of [ 17288-32-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338-P310UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17288-32-3 ]

  • Upstream synthesis route of [ 17288-32-3 ]
  • Downstream synthetic route of [ 17288-32-3 ]

[ 17288-32-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 23596-34-1 ]
  • [ 17288-32-3 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogen In ethanol at 35 - 57℃; for 4.00 h; Parr reactor 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester, 4a-1 (Scheme 1, step c)
Add to a 2 L thick-walled Parr reactor compound 3a-1 (56.8 g, 0.24 mol), ethanol (200 proof, 850 mL, 15 parts) and 10percent Pd/C (5.7 g, 10percent by wt.).
Connect the reaction vessel to a Parr hydrogenator, flush with hydrogen and pressurize the orange slurry to 45 psi.
Shake at rt for 1 h during which time the temperature rises to 57° C.
When the temperature of the reaction mixture stabilizes at 35° C., slowly heat the reaction to 40° C. for 3 h.
When the reaction is complete as determined by-TLC (silica gel, 1percent MeOH in CH2Cl2), cool the reaction mixture to rt, filter the slurry through Celite.(R)., and wash the filter cake with EtOH (4*200 mL).
Concentrate the yellow filtrate to afford a solid (41.6 g), add ethyl acetate (302 mL) and heat on a steam bath.
Cool the mixture to rt and add heptane (600 mL) to precipitate the product.
Stir the mixture in an ice bath for 1 h, filter and wash the filter cake with heptane (100 mL).
Dry the filter cake (50° C./0.1 in Hg) for 24 h to give 4a-1 as a light gray solid (36.6 g, 81percent yield).
1H NMR (DMSO-d6) 1.36 (t, 3H, J=7.0 Hz), 4.36 (q, 2H, J=7.0 Hz), 7.19 (s, 1H), 7.25 (dd, 1H, J=4.5, 8.1 Hz), 7.82 (d, 1H, J=8.1 Hz), 8.44 (d, 1H, J=4.5 Hz), δ 12.11 (s, 1H).
81% With titanium tetrachloride; tin(ll) chloride In ethanol for 4.00 h; Heating / reflux Hydrogenate 3a-1 (20 g) over 10percent palladium on carbon (5.5 g) in EtOH (350 mL) at rt for 3 hours under 1200 psi. Filter the reaction mixture through Celite.(R). and concentrate the filtrate to give ester 4a-1 (R4H) in 39percent yield. Alternatively, reduce 3a-1 with SnCl2 (5.0 equiv), TiCl4 (2.5 equiv) in EtOH at reflux for 4 h, cool to ambient temperature, concentrate and purify by silica gel chromatography to provide ester 4a-1 (R4H) in 81percent yield. 1H NMR (DMSO-d6) δ 13.48 (bs, 1H), 8.80 (dd, 1H, J=0.7, 5.4 Hz), 8.56 (dd, 1H, J=0.7, 8.4 Hz), 7.80 (dd, 1H, J=5.5, 8.4 Hz), 7.37 (s, 1H), 4.40 (q, 2H, J=7.0 Hz), 1.38 (t, 3H, J=7.0 Hz).
39% With hydrogen In ethanol at 20℃; for 3.00 h; Hydrogenate 3a-1 (20 g) over 10percent palladium on carbon (5.5 g) in EtOH (350 mL) at rt for 3 hours under 1200 psi. Filter the reaction mixture through Celite.(R). and concentrate the filtrate to give ester 4a-1 (R4H) in 39percent yield. Alternatively, reduce 3a-1 with SnCl2 (5.0 equiv), TiCl4 (2.5 equiv) in EtOH at reflux for 4 h, cool to ambient temperature, concentrate and purify by silica gel chromatography to provide ester 4a-1 (R4H) in 81percent yield. 1H NMR (DMSO-d6) δ 13.48 (bs, 1H), 8.80 (dd, 1H, J=0.7, 5.4 Hz), 8.56 (dd, 1H, J=0.7, 8.4 Hz), 7.80 (dd, 1H, J=5.5, 8.4 Hz), 7.37 (s, 1H), 4.40 (q, 2H, J=7.0 Hz), 1.38 (t, 3H, J=7.0 Hz).
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Patent: US2005/131012, 2005, A1. Location in patent: Page/Page column 14
[3] Patent: US2005/131012, 2005, A1. Location in patent: Page/Page column 14
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 339 - 342
[5] Patent: US2005/131012, 2005, A1. Location in patent: Page/Page column 14
  • 2
  • [ 17288-30-1 ]
  • [ 17288-32-3 ]
Reference: [1] Patent: WO2004/104001, 2004, A2. Location in patent: Page 42
[2] Patent: US2007/259910, 2007, A1. Location in patent: Page/Page column 10
  • 3
  • [ 677302-64-6 ]
  • [ 17288-32-3 ]
YieldReaction ConditionsOperation in experiment
86% With iron; acetic acid In ethanol for 2.00 h; Heating / reflux INTERMEDIATE 14 Ethyl pyrrolo[3,2-b]pyridine-2-carboxylate A mixture of Intermediate 13 (6.30 g, 26.5 mmol) and iron powder (325 mesh, 13.3 g, [238.] 2 mmol) in [ETOH] (100 [ML)] and [ACOH] (100 [ML)] was heated at reflux for 2 [H.)] Volatiles were removed in vacuo and toluene used to azeotrope excess [ACOH] (3 x 100 ml). The brown residue was suspended in EtOAc and passed through a plug of silica gel, eluting the desired product with EtOAc. Concentration of the eluent in vacuo gave the title compound as an off-white solid (4.32 g, 86percent). [8H] (d3-MeOD) [8.] [33-8.] 30 [(1H,] m), 7.84-7. 80 [(1H,] m), 7.22 [(1H,] dd, [J4.] 6,8. 4 Hz), 7.14 (1H, d, [J0.] 9 Hz), 4.33 (2H, q, J7.1 Hz), 1.33 (3H, t, J7.1 Hz). LCMS Method C [(: EST] RT 1.22 minutes, 191 [(M+H).]
Reference: [1] Patent: WO2004/31188, 2004, A1. Location in patent: Page 43
  • 4
  • [ 617-35-6 ]
  • [ 6298-19-7 ]
  • [ 17288-32-3 ]
YieldReaction ConditionsOperation in experiment
190 mg
Stage #1: at 20℃; for 24.00 h;
Stage #2: at 160℃; for 0.33 h; Microwave irradiation
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] Angewandte Chemie - International Edition, 2016, vol. 55, # 39, p. 11859 - 11862[2] Angew. Chem., 2016, vol. 128, p. 12038 - 12041,4
[3] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 660 - 668
  • 5
  • [ 64-17-5 ]
  • [ 17288-35-6 ]
  • [ 17288-32-3 ]
Reference: [1] Patent: WO2018/119395, 2018, A1. Location in patent: Page/Page column 134; 135
[2] Patent: WO2018/195075, 2018, A1. Location in patent: Page/Page column 55; 100; 101
  • 6
  • [ 2999-46-4 ]
  • [ 206181-90-0 ]
  • [ 17288-32-3 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2036 - 2039
  • 7
  • [ 18699-87-1 ]
  • [ 17288-32-3 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 339 - 342
[3] Patent: WO2004/104001, 2004, A2
[4] Patent: US2007/259910, 2007, A1
  • 8
  • [ 5470-18-8 ]
  • [ 17288-32-3 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 339 - 342
[3] Patent: WO2004/104001, 2004, A2
  • 9
  • [ 2999-46-4 ]
  • [ 405174-97-2 ]
  • [ 17288-32-3 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2036 - 2039
  • 10
  • [ 64362-41-0 ]
  • [ 17288-32-3 ]
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1040 - 1045
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 339 - 342
  • 11
  • [ 617-35-6 ]
  • [ 17288-32-3 ]
Reference: [1] Synthesis, 2005, # 15, p. 2571 - 2577
  • 12
  • [ 6298-19-7 ]
  • [ 17288-32-3 ]
Reference: [1] Synthesis, 2005, # 15, p. 2571 - 2577
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