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Product Details of [ 487-89-8 ]

CAS No. :487-89-8 MDL No. :MFCD00005622
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :OLNJUISKUQQNIM-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :10256
Synonyms :
3-Formylindole;Indole-3-formaldehyde;NSC 10118;β-Indolylaldehyde

Calculated chemistry of [ 487-89-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
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 : 43.69
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) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.12
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 2.69
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.464 mg/ml ; 0.0032 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 0.828 mg/ml ; 0.0057 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.21
Solubility : 0.0897 mg/ml ; 0.000618 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 487-89-8 ]

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:

Applications of [ 487-89-8 ]

Indole-3-carboxaldehyde (CAS: 487-89-8) can be used in the preparation of Indole-3-carbinol (CAS: 700-06-1). ndole-3-carbinol (I3C) suppresses NF-κB activity while acting as an agonist for the Aryl hydrocarbon receptor (AhR) and inhibiting WWP1 (WW domain-containing ubiquitin E3 ligase 1).

Application In Synthesis of [ 487-89-8 ]

* 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 [ 487-89-8 ]
  • Downstream synthetic route of [ 487-89-8 ]

[ 487-89-8 ] Synthesis Path-Upstream   1~33

  • 1
  • [ 487-89-8 ]
  • [ 141-82-2 ]
  • [ 1204-06-4 ]
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[2] Journal of Organic Chemistry, 1958, vol. 23, p. 1171,1176
[3] Journal of Biological Chemistry, 1934, vol. 104, p. 675,677
[4] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 2202,2209; engl. Ausg. S. 2287, 2294
  • 2
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  • [ 1204-06-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 1994, vol. 29, # 11, p. 903 - 906
  • 3
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  • [ 5416-80-8 ]
Reference: [1] Heterocycles, 2007, vol. 73, # C, p. 537 - 554
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  • [ 5416-80-8 ]
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Reference: [1] Heterocycles, 2007, vol. 73, # C, p. 537 - 554
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  • [ 119910-45-1 ]
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Reference: [1] Heterocycles, 2007, vol. 73, # C, p. 537 - 554
  • 6
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  • [ 876-72-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3696 - 3708
  • 7
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  • [ 1670-85-5 ]
Reference: [1] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 3006 - 3016
  • 8
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  • [ 6245-89-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 13, p. 4032 - 4035[2] Angew. Chem., 2015, vol. 127, # 13, p. 4104 - 4107,4
  • 9
  • [ 487-89-8 ]
  • [ 16502-01-5 ]
Reference: [1] Medicinal Chemistry Research, 2017, vol. 26, # 12, p. 3173 - 3187
[2] Patent: CN108623585, 2018, A,
  • 10
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  • [ 27018-76-4 ]
Reference: [1] Journal of the Chilean Chemical Society, 2011, vol. 56, # 4, p. 866 - 869
  • 11
  • [ 141692-10-6 ]
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  • [ 4771-48-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 3, p. 1322 - 1326
  • 12
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  • [ 4771-48-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 3, p. 1322 - 1326
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 3, p. 1322 - 1326
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  • [ 59020-09-6 ]
  • [ 4771-48-6 ]
  • [ 108378-88-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 3, p. 1322 - 1326
  • 15
  • [ 487-89-8 ]
  • [ 877-03-2 ]
  • [ 17826-04-9 ]
  • [ 17900-95-7 ]
Reference: [1] Environmental Toxicology and Chemistry, 2001, vol. 20, # 3, p. 589 - 596
  • 16
  • [ 487-89-8 ]
  • [ 877-03-2 ]
  • [ 17826-04-9 ]
Reference: [1] Journal of Chemical Ecology, 1997, vol. 23, # 11, p. 2507 - 2521
  • 17
  • [ 487-89-8 ]
  • [ 75-18-3 ]
  • [ 39974-94-2 ]
Reference: [1] Asian Journal of Chemistry, 2013, vol. 25, # 15, p. 8741 - 8748
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  • [ 57476-50-3 ]
YieldReaction ConditionsOperation in experiment
100% With dmap; triethylamine In dichloromethane at 20℃; for 0.5 h; Inert atmosphere General procedure: To a solution of indole-3-carboxaldehyde, triethylamine (1.3 equiv.), and 10 mol percent DMAP in CH2Cl2 was added Boc2O (1.2 equiv.). The reaction was stirred at room temperature until the starting material was completely consumed. The reaction was diluted with CH2Cl2, worked up with water. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EA/nHx =1:5 for 1a, 1b; EA/nHx = 1:9 for 1c) to give compounds 1a-1c.
99% With dmap In acetonitrile at 20℃; To a solution of 1H-indole-3-carbaldehyde (500 mg, 3.44 mmol) in anhydrous acetonitrile (12 mL) at room temperature was added DMAP (84 mg, 0.69 mmol) and then Boc2O (1.13 g, 5.17 mmol). The mixture was stirred at room temperature overnight and then solvent was removed under reduced pressure. Residue was purified by column chromatography (EtOAc/cyclohexane, 1:1) to give 21 (840 mg, 3.42 mmol, 99percent) as a beige solid. Mp = 116-117 °C; IR (ATR): 1741, 1676, 1451, 1397, 1134 cm-1; 1H NMR (400 MHz, DMSO-d6): 1.66 (s, 9H, 3CH3 Boc), 7.38-7.47 (m, 2H), 8.14 (2d, 2H, J = 7.6 Hz), 8.67 (s, 1H), 10.08 (s, 1H, CHO); 13C NMR (100 MHz, DMSO-d6): 27.4 (3CH3 Boc), 85.4 (C Boc), 114.9 (CH), 120.6 (C), 121.3 (CH), 124.4 (CH), 125.5 (C), 125.8 (CH), 135.2 (C), 138.2 (CH), 148.2 (CO Boc), 187.0 (CO aldehyde); HRMS (ESI+) calcd for C14H15NNaO3 (M + Na)+ 268.0950, found 268.0963.
99% With dmap In acetonitrile at 25℃; for 1.5 h; Inert atmosphere Into a 250 mL round bottom flask charged with a stirbar, 5 g (34.4 mmol, 1.0 equiv.) indole-3-carbaldehyde, and 115 mL MeCN was added 9.77 g (44.8 mmol, 1.3 equiv.) Boc2O followed by 1.40 g (11.5 mmol, 0.33 equiv.) DMAP. The reaction mixture was stirred for 90 minutes, then was partitioned between 250 mL CH2Cl2and 250 mL deionized H2O. The organic layer was removed, and the residual product was extracted from the aqueous layer with an additional 150 mL CH2Cl2. The combined organic layers were washed twice with 250 mL deionized water then brine, then were concentrated to furnish 8.43g (>99percent) N-Boc-indole-3-carbaldehyde. Rf = 0.60, 70 : 30 = Hex :EtOAc, stain = I2, Dragendorff-Munier, 2,4-DNP, PMA. 1HNMR (400 MHz, CDCl3): δ 10.06 (s, 1H), 8.26 (d, J = 8.3 Hz, 1H), 8.19 (s, 1H), 8.12 (d, J = 8.0 Hz, 1H), 7.37 (m, 2H), 1.70 (s, 9H). 13C NMR (101 MHz, CDCl3): δ 185.7, 148.7, 136.5, 135.9, 126.1, 126.0, 124.5, 122.1, 121.5, 115.2, 85.6, 28.1. Mass: LRMS (ESI+) m/z calcd for [M+Na]+ 268.1, found 268.1.
99% at 80℃; for 0.5 h; Green chemistry General procedure: The reactions were carried out in a 50 mL RB flask under reduced pressure for 10 min at 80°C unless reported differently. In a typical experiment, 5 mmol of amine was added to 5 mmol of BOC anhydride, and the reaction was allowed to proceed for 10 min. The desired product was obtained in a rotary evaporator under vacuum conditions.
99% With dmap; triethylamine In dichloromethane for 0.5 h; 3-indole formaldehyde (435 mg, 3 mmol) was dissolved in dichloromethane (15 mL). Add DMAP (4 mg, 0.03 mmol), triethylamine (606 mg, 6 mmol) and Boc 2 O (1.3 g, 6 mmol). TLC spot plate monitoring (petroleum ether / EtOAc = 2:1 as developing solvent, starting material Rf = 0.24, new point Rf = 0.79). After 30 minutes, the starting material was completely reacted. The reaction solution was directly concentrated by rotary evaporation to remove most of Boc2O (b.p. 57 ° C). Purification by column chromatography on silica gel (300-400 mesh), petroleum ether / EtOAc (10:1) as eluent, Rotary evaporation gave 728 mg of white crystals (36b) with a yield of 99percent.
96% With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2 h; Inert atmosphere To a stirred solution of compound U8 (5.00 grams, 34.5 mmol) in DCM (50 ml) was added DMAP (2.10 grams, 17.3 mmol) and DIEA (9.0 mlL, 51.7 mmol) and Boc2O (11.3 grams, 51.7 mmol). The mixture was stirred for 2 hours at room temperature under N2 atmosphere, washed with 1N HCl (100 ml×2), saturated NaHCO3 solution (100 ml×2) and brine (80 ml), the organic phase was dried over Na2SO4, concentrated and purified by flash chromatography on silica gel (PE/EtOAc=30:1-10:1-4:1) to give compound U9 (8.10 grams, 96percent) as a white solid. (0367) 1HNMR (400 MHz, CDCl3): δ=1.74 (s, 9H), 7.40-7.45 (m, 2H), 8.17-8.19 (m, 1H), 8.27 (s, 1H), 8.31-8.33 (m, 1H), 10.13 (s, 1H).
96% With dmap; triethylamine In dichloromethane at 25℃; for 12 h; Inert atmosphere According to the literature,18 di-tert-butyl dicarbonate (2.6 g,12.0 mmol) and Et3N (1.8 mL, 13.0 mmol), followed by DMAP (122 mg, 1.00 mmol) were added to a solution of indole-3-carboxaldehyde (1.5 g, 10.0 mmol) in anhyd CH2Cl2 (50 mL). The reaction mixture was then stirred at 25 °C for 12 h. The resulting mixture was diluted with CH2Cl2 and washed with sat. aq NH4Cl (50 mL). The product was extracted with CH2Cl2(2 × 80 mL) and 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) yielding tert-butyl 3-formyl-1H-indole-1-carboxylateas a white solid (2.3 g, 96percent).1H NMR (400 MHz, CDCl3): δ = 10.11 (s, 1H), 8.29-8.32 (m, 1H), 8.23(s, 1H), 8.14 (d, J = 7.5 Hz, 1H), 7.45-7.30 (m, 2H), 1.71 (s, 9H).
90% With dmap; triethylamine In dichloromethane at 0 - 20℃; Example 1: 3-((lH-Indol-3-yl)methoxy)-5-butylphenyl (2-(4-methylpiperazin-l- yPethyPcarbamate [0082] Step 1. To a solution of lH-indole-3-carbaldehyde (29.2 g, 0.2 mol), 4- (dimethylamino)pyridine (1.28 g, 0.01 mol), and triethylamine (30.3 g, 0.3 mol) in dichloromethane (100 mL) was added dropwise di-tert-butyl dicarbonate (Boc20) (65.2 g, 0.2 mol) at 0 °C. The mixture was stirred at room temperature overnight. Dichloromethane (100 mL) was added and the organic layer was washed with 0 (3 x 50 mL) and brine (50 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give tert- butyl 3-formyl-lH-indole-l-carboxylate (44 g, 90percent). 1H NMR (400 MHz, CDC13) δ: 1.71 (s, 9H), 7.44-7.25 (m, 2H), 8.15 (d, 1H), 8.24 (s, 1H), 8.29 (d, 1H), 10.1 (s, 1H).
80% With dmap In tetrahydrofuran; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran Example 2
N-Boc-Indole-3-carboxaldehyde
To a 500 mL round bottom flask containing a solution of crude indole-3-carboxaldehyde (0.5 mol) in 300 mL of DCM was added 6.1 g (0.05 mol) of 4-dimethylaminopyridine.
The reaction mixture was cooled to 0° C. and 600 mL of a solution of di-tert-butyldicarbonate (1.0 M in THF) was added slowly dropwise via an addition funnel.
The reaction mixture was allowed to warm to room temperature for 6 h.
The reaction mixture was quenched with 1.0 L of water and the organic layer separated.
The organic layer was washed with 5percent HCl (2*1.0 L) and sat. NaCl (1.0 L), dried (MgSO4), filtered, and concentrated in vacuo.
The crude solid was purified by dissolving it in DCM (~1.0 L) and precipitating it by the addition of hexanes (~1.0 L) and filtering with a fritted funnel.
The filter cake was washed with hexanes and dried in vacuo to give N-Boc-indole-3-carboxaldehyde (80-85percent yield).
80% With dmap In tetrahydrofuran; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran STR49 N-Boc-Indole-3-carboxaldehyde
To a 500 mL round bottom flask containing a solution of crude indole-3-carboxaldehyde (0.5 mol) in 300 mL of DCM was added 6.1 g (0.05 mol) of 4-dimethylaminopyridine.
The reaction mixture was cooled to 0° C. and 600 mL of a solution of di-tert-butyldicarbonate (1.0 M in THF) was added slowly dropwise via an addition funnel.
The reaction mixture was allowed to warm to room temperature for 6 h.
The reaction mixture was quenched with 1.0 L of water and the organic layer separated.
The organic layer was washed with 5percent HCl (2*1.0 L) and sat. NaCl (1.0 L), dried (MgSO4), filtered, and concentrated in vacuo.
The crude solid was purified by dissolving it in DCM (~1.0 L) and precipitating it by the addition of hexanes (~1.0 L) and filtering with a fritted funnel.
The filter cake was washed with hexanes and dried in vacuo to give N-Boc-indole-3-carboxaldehyde (80-85percent yield).
80% With dmap In tetrahydrofuran; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran EXAMPLE 2
N-Boc-Indole-3-carboxaldehyde
To a 500 mL round bottom flask containing a solution of crude indole-3-carboxaldehyde (0.5 mol) in 300 mL of DCM was added 6.1 g (0.05 mol) of 4-dimethylaminopyridine.
The reaction mixture was cooled to 0° C. and 600 mL of a solution of di-tert-butyldicarbonate (1.0 M in THF) was added slowly dropwise via an addition funnel.
The reaction mixture was allowed to warm to room temperature for 6 h.
The reaction mixture was quenched with 1.0 L of water and the organic layer separated.
The organic layer was washed with 5percent HCl (2*1.0 L) and sat. NaCl (1.0 L), dried (MgSO4), filtered, and concentrated in vacuo.
The crude solid was purified by dissolving it in DCM (Q1.0 L) and precipitating it by the addition of hexanes (-1.0 L) and filtering with a fritted funnel.
The filter cake was washed with hexanes and dried in vacuo to give N-Boc-indole-3-carboxaldehyde (80-85percent yield).
80% With dmap In tetrahydrofuran; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran EXAMPLE 2
N-Boc-Indole-3-carboxaldehyde
To a 500 mL round bottom flask containing a solution of crude indole-3-carboxaldehyde (0.5 mol) in 300 mL of DCM was added 6.1 g (0.05 mol) of 4-dimethylaminopyridine.
The reaction mixture was cooled to 0° C. and 600 mL of a solution of di-tert-butyldicarbonate (1.0 M in THF) was added slowly dropwise via an addition funnel.
The reaction mixture was allowed to warm to room temperature for 6 h.
The reaction mixture was quenched with 1.0 L of water and the organic layer separated.
The organic layer was washed with 5percent HCl (2*1.0 L) and sat. NaCl (1.0 L), dried (MgSO4), filtered, and concentrated in vacuo.
The crude solid was purified by dissolving it in DCM (~1.0 L) and precipitating it by the addition of hexanes (~1.0 L) and filtering with a fritted funnel.
The filter cake was washed with hexanes and dried in vacuo to give N-Boc-indole-3-carboxaldehyde (80-85percent yield).
6.1 g With dmap In acetonitrile at 20℃; General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification. ferf-Butyl 3-formyl-1 /-/-indole-1-carboxylate was prepared according to general procedure F from 1 /-/-indole-3-carbaldehyde (3.770 g; 25.97 mmol), di-ferf-butyl dicarbonate (6.800 g; 31.16 mmol) and DMAP (0.317 g; 2.595 mmol) in acetonitrile (70 mL) to afford 6.100 g (96percent) of the desired compound as a yellow solid. 1H NMR (DMSO-c6) δ 10.09 (1 H, s); 8.66 (1 H, s); 8.15 (2H, dd); 7.32-7.53 (2H, m); 1.68 (9H, s).

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YieldReaction ConditionsOperation in experiment
97.7% With tetrabutylammomium bromide In tetrahydrofuran (1)
1-(tert-Butyloxycarbonyl)-3-formylindole
Indole-3-carboxaldehyde (4.53 g, 30 mmol) was dissolved in tetrahydrofuran (100 mL) (dissolved at about 40° C.).
Aqueous potassium hydroxide (1N, 30 mL) and tetrabutylammonium bromide (0.97 g, 3 mmol) were added.
Then di-t-butylcarbonate (7.2 g, 33 mmol) was added (the temperature should not rise about 25° C.).
The resulting mixture was stirred at room temperature until the starting material was not detected by TLC (CH2 CL2 /CH3 OH 9:1).
The reaction mixture was separated, and the aqueous layer was extracted with ethyl acetate (2*50 mL).
The combined organic layer was dried with MgSO4 and evaporated to give crude product.
The product was recrystallized from methylene chloride/hexane (20 mL/100 mL) to obtain needle crystals (7.19 g, 97.7percent).
m.p. 124°-125° C.
Reference: [1] Patent: US5554753, 1996, A,
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[2] Liebigs Annalen der Chemie, 1985, # 2, p. 413 - 417
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YieldReaction ConditionsOperation in experiment
97%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Cooling with ice
Stage #2: at 20℃;
NaH (60percent dispersion in mineral oil, 40.00 mmol, 0.96 g) was added portionwise to a stirred solution of indole-3-carboxaldehyde 11 (20.00 mmol, 2.90 g) in anhydrous THF (50 mL) cooled in an ice bath, then slowly allowed to warm to r.t. After stirring for 30 min PhSO2Cl (24.00 mmol, 4.24 g) in anhydrous THF was added dropwise. When TLC monitoring showed that the starting material 11 had disappeared, the reaction mixture was evaporated under reduced pressure to remove the solvent and then diluted with ice water (300 mL). Solid products were filtrated off and recrystallized from acetone/petroleum ether (60-90 °C) to give the desired intermediate 12 in a yield of 97percent, mp 151-153 °C 1H NMR (600 MHz, CDCl3): δ: 7.37 (t, J = 7.2 Hz, 1H), 7.42 (dd, J = 11.4, 4.2 Hz, 1H), 7.52 (t, J = 7.8 Hz, 2H), 7.62 (t, J = 7.2 Hz, 1H), 7.97 (t, J = 7.8 Hz, 3H), 8.20-8.31 (m, 2H), 10.11 (s, 1H). HRMS (MALDI): m/z 286.0515. Calcd. C15H11NO3S: 286.0538 [M + H]+.
33%
Stage #1: With potassium hydroxide In ethanol
Stage #2: for 0.5 h;
To a solution of indole 3-carboxaldehyde (8y) (100 mmol) in ethanol (500 mL) at RT was added potassium hydroxide (1.1 equiv). The mixture was stirred until total solubilization. The ethanol was completely removed in vacuum and the residual was dissolved in acetone (250 mL) followed by adding benzenesulfonyl chloride (1.1 equiv, 110 mmol). The reaction mixture was stirred for half hour. The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 33percent. 1H NMR (500 MHz, CDCI3) δ 10.17 (s, 1 H), 8.25-8.39 (m, 2 H), 7.97-8.09 (m, 3 H), 7.69 (t, 7 = 7.33 Hz, 1 H), 7.59 (t, 7 = 7.5 Hz, 2 H), 7.39 - 7.54 (m, 2 H). MS (ESI) calcd for C15H11NO3S 285.1, found 286.0 [M + H]+.
33% With potassium hydroxide In ethanol; acetone at 20℃; for 0.5 h; To a solution of indole 3-carboxaldehyde (8y) (100 mmol) in ethanol (500 mL) at RT was added potassium hydroxide (1.1 equiv). The mixture was stuffed until total solubilization. The ethanol was completely removed in vacuum and the residual was dissolved in acetone (250 mL) followed by adding benzenesulfonyl chloride (1.1 equiv, 110 mmol). The reaction mixture was stuffed forhalf hour. The precipitate was filtered off and the filtrate was concentrated and recrystallized from methanol to give a white solid. Yield: 33percent. ‘H NMR (500 MHz, CDC13) ö 10.17 (s, 1 H), 8.25-8.39 (m, 2 H), 7.97-8.09 (m, 3 H), 7.69 (t, J= 7.33 Hz, 1 H), 7.59 (t, J= 7.5 Hz, 2 H), 7.39 -7.54 (m, 2 H). MS (ESI) calcd for C,5H,,N035 285.1, found 286.0 [M + Hf’.
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