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[ CAS No. 27257-15-4 ] {[proInfo.proName]}

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Chemical Structure| 27257-15-4
Chemical Structure| 27257-15-4
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Product Details of [ 27257-15-4 ]

CAS No. :27257-15-4 MDL No. :MFCD09743451
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZVOCBNCKNQJAFL-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :583068
Synonyms :

Calculated chemistry of [ 27257-15-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.0
TPSA : 17.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 1.57
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.49
Consensus Log Po/w : 1.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.12
Solubility : 1.0 mg/ml ; 0.0076 mol/l
Class : Soluble
Log S (Ali) : -1.23
Solubility : 7.73 mg/ml ; 0.0585 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.483 mg/ml ; 0.00366 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 27257-15-4 ]

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

Application In Synthesis of [ 27257-15-4 ]

* 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 [ 27257-15-4 ]
  • Downstream synthetic route of [ 27257-15-4 ]

[ 27257-15-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 271-63-6 ]
  • [ 74-88-4 ]
  • [ 27257-15-4 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h; Inert atmosphere
Stage #2: for 1 h; Inert atmosphere
General procedure: The preparation of the known compound 1a: A dried round-bottomed flask equipped with a magnetic stirring bar was charged with 7-azaindole (2 g, 16.95 mmol) and DMF (10 mL) under a nitrogen atmosphere. The mixture was cooled to 0 °C, NaH (1.2 equiv) was added and stirring continued for 1 h. Then, methyl iodide (1.1 equiv) was added and the mixture was stirred for another 1 h. Afterwards the reaction was quenched with ice cold water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure to give N-methyl-7-azaindoles in a quantitative yield [3].
96%
Stage #1: With Tris(3,6-dioxaheptyl)amine; potassium <i>tert</i>-butylate In toluene at 0 - 20℃; for 3 h;
Stage #2: at 0 - 20℃; for 1 h;
General procedure: To a cold solution of appropriate pyrrolo-pyridines 8a,c,e (2.5 mmol) in anhydrous toluene (25 mL), t-BuOK (0.38 g, 3.4 mmol) and TDA-1 (1 or 2 drops) were added at 0 °C. The reaction mixture was stirred at room temperature for 3 h and then MeI (2.5 mmol, 0.2 mL) was added at 0 °C. TLC analysis (ethyl acetate) revealed that methylation was complete after 1 h. The solvent was evaporated under reduced pressure. The residue was treated with water, extracted with DCM (3 × 20 mL), dried (Na2SO4), evaporated and purified by column chromatography using DCM/ethyl acetate (9/1) as eluent to give derivatives 8b,d,f [42].
85%
Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5 h;
Stage #2: at 20℃;
a) 1-Methyl-lH-pyrrolo [2, 3-b] pyridine; lH-Pyrrolo [2, 3-b] pyridine (1.00 g, 8.46 mmol) was dissolved in 10 mL of DMF and cooled on an ice bath. NaH (0.203 g, 8.47 mmol) was added and after 30 min methyl iodide (0.527 mL, 8.47 mmol) was added. The reaction mixture was stirred overnight at room temperature and then poured into 100 mL of water, extracted three times with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated and a clean product was obtained. Yield: 0.950 g (85percent). 'H NMR (300 MHz, CDC13) 88. 34 (dd, 1H), 7.90 (dd, 1H), 7.18 (d, 1H), 7.05 (dd, 1H), 6.45 (d, 1H), 3.90 (s, 3H).
Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 309 - 313
[2] Green Chemistry, 2017, vol. 19, # 23, p. 5559 - 5563
[3] Organic Letters, 2013, vol. 15, # 22, p. 5718 - 5721
[4] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 2, p. 255 - 267
[5] Journal of Natural Products, 2009, vol. 72, # 12, p. 2199 - 2202
[6] ChemMedChem, 2011, vol. 6, # 7, p. 1300 - 1309
[7] Marine Drugs, 2015, vol. 13, # 1, p. 460 - 492
[8] Angewandte Chemie - International Edition, 2017, vol. 56, # 14, p. 3961 - 3965[9] Angew. Chem., 2017, vol. 129, # 14, p. 4019 - 4023,5
[10] Heterocycles, 2000, vol. 53, # 5, p. 1145 - 1150
[11] ChemBioChem, 2010, vol. 11, # 3, p. 305 - 314
[12] Heteroatom Chemistry, 2011, vol. 22, # 2, p. 148 - 157
[13] Organic Letters, 2004, vol. 6, # 17, p. 2897 - 2900
[14] Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8050 - 8057
[15] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[16] Patent: WO2005/66132, 2005, A1, . Location in patent: Page/Page column 65-66
[17] Archiv der Pharmazie, 2018, vol. 351, # 10,
[18] Helvetica Chimica Acta, 2008, vol. 91, # 9, p. 1787 - 1797
[19] Journal of Physical Chemistry, 1993, vol. 97, # 9, p. 1770 - 1780
[20] Journal of Medicinal Chemistry, 1992, vol. 35, # 1, p. 177 - 184
[21] Patent: EP1452525, 2004, A1, . Location in patent: Page 20
[22] Chemistry - A European Journal, 2011, vol. 17, # 35, p. 9581 - 9585
[23] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 3, p. 1201 - 1212
[24] Organic Letters, 2013, vol. 15, # 8, p. 2034 - 2037
[25] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5115 - 5129
[26] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 7060 - 7072
[27] Marine Drugs, 2016, vol. 14, # 12,
  • 2
  • [ 74-88-4 ]
  • [ 27257-15-4 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With sodium hydride In N,N-dimethyl-formamide for 0.5 h;
Stage #2: for 1 h;
To a solution of lH-pyrrolo[2,3-b]pyridine (1.00 g, 8.46 mmol)and DMF (10 mL) is added 60percent NaH (0.41 g, 10.16 mmol). After 30 min, MeI (0.63 mL, 10.16 mmol) is added and the solution stirred for 1 h. The solution is diluted with EtOAc (60 mL), washed with water (2 X 50 mL), brine (50 mL), dried aver MgSO4, filtered and concentrated to furnish the title compound (1.10 g, 0.83 mmol, 99percent). 1H NMR (CDCl3), δ 3.90 (s, 3H), 6.45 (d, J = 3.5 Hz, IH), 7.05 (dd, 7 = 8.1, 4.6 Hz, IH), 7.17 (d, J = 3.5 EPO <DP n="65"/>Hz, IH), 7.90 (d, J = 7.7, 1.8 Hz, IH), 8.40 (dd, J = 4.8, 1.3 Hz, IH). LC/MS (m/z): calcd. for C8H8N2 (M+H)+: 133.2; found:.
Reference: [1] Patent: WO2006/107784, 2006, A1, . Location in patent: Page/Page column 63-63
  • 3
  • [ 271-63-6 ]
  • [ 62018-65-9 ]
  • [ 74-88-4 ]
  • [ 27257-15-4 ]
Reference: [1] Patent: EP1346982, 2003, A1,
  • 4
  • [ 271-63-6 ]
  • [ 27257-15-4 ]
Reference: [1] Patent: EP1226138, 2004, B1,
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 2573,2577
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 6554,6556
[4] Chemical Communications, 2013, vol. 49, # 23, p. 2368 - 2370
  • 5
  • [ 77-78-1 ]
  • [ 55052-24-9 ]
  • [ 332875-32-8 ]
  • [ 27257-15-4 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1357 - 1360
  • 6
  • [ 27257-15-4 ]
  • [ 68-12-2 ]
  • [ 171919-36-1 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: at 0℃; for 0.166667 h;
Stage #2: at 0 - 60℃; for 1.51667 h;
Stage #3: With sodium hydrogencarbonate In water
b) 1-Methyl-lH-pyrrolo [2, 3-b] pyridine-3-carbaldehyde; POC13 (1.2 g, 7.9 mmol) was added dropwise with stirring to 10 mL of DMF at 0°C. After stirring 10 min a solution of 1-methyl-lH-pyrrolo [2, 3-b] pyridine (0.95 g, 7. 2 mmol) in 5 mL of DMF was added during 1 min. The reaction mixture was stirred for lh at 0°C and a further 30 min at 60°C. It was poured into water which was made alkaline with NaHC03 (aq) and extracted 3 times with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product (0.85 g, 74percent) was sufficiently pure to be used in the subsequent step below. 'H NMR (300 MHz, CDC13) No. 9. 97 (s, 1H), 8.55 (m, 1H), 8.44 (m, 1H), 7.84 (s, 1H), 7.27 (m, 1H), 3.97 (s, 3H).
Reference: [1] Chemical and pharmaceutical bulletin, 1995, vol. 43, # 8, p. 1351 - 1357
[2] Patent: WO2005/66132, 2005, A1, . Location in patent: Page/Page column 66
[3] Heteroatom Chemistry, 2011, vol. 22, # 2, p. 148 - 157
[4] Patent: WO2009/3003, 2008, A2, . Location in patent: Page/Page column 61-62
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 3, p. 1201 - 1212
  • 7
  • [ 110-18-9 ]
  • [ 27257-15-4 ]
  • [ 171919-36-1 ]
YieldReaction ConditionsOperation in experiment
60% With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products.
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 13, p. 2438 - 2442
[2] Tetrahedron Letters, 2014, vol. 55, # 41, p. 5618 - 5621
  • 8
  • [ 27257-15-4 ]
  • [ 171919-36-1 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydrogencarbonate; trichlorophosphate In ethyl acetate; N,N-dimethyl-formamide (Step 2)
Synthesis of 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde
Phosphoryl chloride (5.15 ml, 55.3 mmol) was added dropwise to DMF (70 ml) under stirring at 0OEC.
After the reaction mixture was stirred at 0OEC for 10 minutes, a solution of 1-methyl-1H-pyrrolo(2,3-b)pyridine (4.87 g, 36.8 mmol) in DMF (5 ml) was added dropwise at the same temperature.
After completion of the dropwise addition, the reaction mixture was stirred at 0OEC for 4 hours and at 60OEC for 3.5 hours.
The reaction mixture was poured in ice water - a saturated aqueous solution of sodium bicarbonate to neutralize the mixture therewith, followed by extraction with chloroform.
The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent.
The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, 1-methyl-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde (4.87 g, 83percent) was obtained as a yellow solid.
1H-NMR (CDCl3) δ: 3.98 (s, 3H), 7.28 (dd, J=7.8,4.7Hz, 1H), 7.85 (s, 1H), 8.44 (d, J=4.7Hz, 1H), 8.55 (d, J=7.8Hz, 1H), 9.97 (s, 1H).
MS (ESI) m/z 160 (M+-H).
Reference: [1] Patent: EP1346982, 2003, A1,
[2] Patent: EP1226138, 2004, B1,
  • 9
  • [ 27257-15-4 ]
  • [ 67-68-5 ]
  • [ 171919-36-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 41, p. 7092 - 7095
  • 10
  • [ 27257-15-4 ]
  • [ 171919-37-2 ]
Reference: [1] Chemical and pharmaceutical bulletin, 1995, vol. 43, # 8, p. 1351 - 1357
  • 11
  • [ 27257-15-4 ]
  • [ 281192-91-4 ]
Reference: [1] Heterocycles, 2000, vol. 53, # 5, p. 1145 - 1150
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