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Chemical Structure| 703-82-2
Chemical Structure| 703-82-2
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Product Details of [ 703-82-2 ]

CAS No. :703-82-2 MDL No. :MFCD06657152
Formula : C9H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :CTNIXLBHXMSZKL-UHFFFAOYSA-N
M.W : 179.60 Pubchem ID :12614669
Synonyms :

Calculated chemistry of [ 703-82-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.7
TPSA : 32.86 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) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.63
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 3.29
Consensus Log Po/w : 2.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.79
Solubility : 0.291 mg/ml ; 0.00162 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.62 mg/ml ; 0.00345 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.85
Solubility : 0.0256 mg/ml ; 0.000143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 703-82-2 ]

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 [ 703-82-2 ]

* 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 [ 703-82-2 ]
  • Downstream synthetic route of [ 703-82-2 ]

[ 703-82-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 703-82-2 ]
  • [ 766557-02-2 ]
Reference: [1] CrystEngComm, 2013, vol. 15, # 37, p. 7490 - 7497
  • 2
  • [ 17422-33-2 ]
  • [ 68-12-2 ]
  • [ 703-82-2 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 0℃; for 1 h;
Stage #2: at 20℃; for 5 h;
Stage #3: With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 0.166667 h;
General procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 °C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 °C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (Na2SO4) and distilled to dryness to give the crude residue, which was purified by flash column chromatography using ethyl acetate/petroleum ether (3:1, v/v) as the eluent to give pure indole-3-carbaldehyde (4a-k).
85%
Stage #1: at 60℃; for 1 h;
Stage #2: With sulfuric acid In water at 50℃; for 1 h;
Example 1:
Step 1: 6-chloro-lH-indole-3-carbaldehvde
[00331] A solution of 6-Chloro-lH-indole (1.0 g, 6.59 mmol) and phosphorus oxychloride (8.56 mmol) in dimethylformamide (12 mL) was heated at 60°C for lh. Water (5 mL) andconcentrated sulfuric acid (3.95 mmol) were added to the reaction mixture then heated at 50°C for 1 h. The mixture was concentrated and the residue was diluted with water (15 mL). The aqueous phase was extracted with ethyl acetate (3 x 25 mL). The organic extracts were combined and concentrated. Purification of the residue over silica gel, 0-75percent ethyl acetate in hexanes, afforded the title compound (1.01 g, 85percent) as a tan solid. LCMS [M+H] calculated: 179.6; observed: 179.9
85%
Stage #1: at 60℃; for 1 h;
Stage #2: With sulfuric acid In water at 50℃; for 1 h;
j00370j A solution of 6-chloro-1H-indole (1.0 g, 6.59 mmol) and POC13 (8.56 mmol) in DMF (12 mL) was heated at 60°C for lh. Water (5 mL) and concentrated sulfuric acid (3.95 mmol) were added and the mixture then heated at 50°C for 1 h. The mixture was concentrated and the residue was diluted with water (15 mL). The aqueous phase was extracted with EtOAc (3 x 25 mL). The organic extracts were combined and concentrated. Purification of the residue over silica gel, 0-75percent EtOAc in hexanes, afforded the title compound (1.01 g, 85percent) as a tan solid. LCMS [M+H]: 179.9
75% at 0 - 20℃; for 3.5 h; A solution of 6-chloroindole (30 mmol) in N,N-dimethylformamide (DMF) (5 mL) was added dropwise to a solution of phosphorus oxychloride (44 mmol) in DMF (32 mL) which had been stirred for 1.5 h at 0°C. The reaction mixture was warmed to room temperature and stirred for 2 h. The solution with the precipitate formed was poured on ice and basified with solid KOH and left overnight. The precipitate was filtered and washed with a mixture of 10percent ethyl acetate in petroleum benzene several times, then left to dry to give the aldehyde. 6-Chloro-1H-indole-3-carbaldehyde (3) Synthesized according to the general procedure of Vilsmeier–Haack reaction; light brick red solid; yield 4.04 g (75percent).

Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 6, p. 1995 - 2004
[2] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[3] Patent: WO2015/42053, 2015, A1, . Location in patent: Paragraph 00331
[4] Patent: WO2016/144704, 2016, A2, . Location in patent: Paragraph 00370
[5] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 1, p. 34 - 41
[6] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1301 - 1305
[7] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1793 - 1798
[8] Journal of the American Chemical Society, 2009, vol. 131, # 12, p. 4214 - 4215
[9] Organic Letters, 2009, vol. 11, # 22, p. 5214 - 5217
[10] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 13, p. 4783 - 4792
[11] Journal of Medicinal Chemistry, 2010, vol. 53, # 14, p. 5155 - 5164
[12] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 1, p. 307 - 310
[13] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 95 - 102
[14] MedChemComm, 2013, vol. 4, # 1, p. 228 - 232
[15] Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3250 - 3254[16] Angew. Chem., 2013, vol. 125, # 11, p. 3332 - 3336,5
[17] Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2362 - 2372
[18] CrystEngComm, 2013, vol. 15, # 37, p. 7490 - 7497
[19] Patent: WO2013/123266, 2013, A1, . Location in patent: Paragraph 00186
[20] Patent: WO2013/123267, 2013, A1, . Location in patent: Paragraph 00220
[21] Organic Letters, 2013, vol. 15, # 24, p. 6262 - 6265
[22] Chemistry - A European Journal, 2014, vol. 20, # 24, p. 7492 - 7500
[23] Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11881 - 11885[24] Angew. Chem., 2014, vol. 126, # 44, p. 12075 - 12079,5
[25] Organic Letters, 2015, vol. 17, # 12, p. 3186 - 3189
[26] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
[27] Synthesis (Germany), 2017, vol. 49, # 11, p. 2562 - 2562
[28] Patent: WO2017/165299, 2017, A2, . Location in patent: Paragraph 0355
[29] Patent: WO2017/205786, 2017, A1, . Location in patent: Paragraph 00394
[30] Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6647 - 6651
[31] Patent: WO2008/119741, 2008, A2, . Location in patent: Page/Page column 64
  • 3
  • [ 17422-33-2 ]
  • [ 110-18-9 ]
  • [ 703-82-2 ]
YieldReaction ConditionsOperation in experiment
72% 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] Tetrahedron Letters, 2014, vol. 55, # 41, p. 5618 - 5621
  • 4
  • [ 17422-33-2 ]
  • [ 298-12-4 ]
  • [ 703-82-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 20, p. 3707 - 3710
  • 5
  • [ 17422-33-2 ]
  • [ 100-61-8 ]
  • [ 703-82-2 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11924 - 11927
  • 6
  • [ 17422-33-2 ]
  • [ 2565-30-2 ]
  • [ 703-82-2 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 19, p. 2353 - 2356
  • 7
  • [ 17422-33-2 ]
  • [ 703-82-2 ]
Reference: [1] Patent: US2005/119260, 2005, A1, . Location in patent: Page/Page column 36
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