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Product Details of [ 944893-74-7 ]

CAS No. :944893-74-7 MDL No. :MFCD09455244
Formula : C11H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :WWOYPVXWHICMOY-UHFFFAOYSA-N
M.W : 173.21 Pubchem ID :17221160
Synonyms :

Safety of [ 944893-74-7 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 944893-74-7 ]

* 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.

  • Downstream synthetic route of [ 944893-74-7 ]

[ 944893-74-7 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 74-96-4 ]
  • [ 1196-69-6 ]
  • [ 944893-74-7 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 1H-indole-5-carboxaldehyde With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 1h; Stage #2: ethyl bromide In dichloromethane at 50℃; for 72h; 2.2 4.1.2.1 1-Ethyl-1H-indole-5-carbaldehyde (1) and 1-methyl-1H-indole-5-carbaldehyde (2) 1.04g (26mmol) of NaOH and 20mg of n-Bu4N+HSO4- were added to a stirred solution of 1H-indole-5-carbaldehyde (2.0g, 13.8mmol) in 40mL of dry CH2Cl2. After 1hat room temperature 3mL (40.2mmol) of ethyl bromide or methyl iodide were added and the reaction was heated at 50°C. After 3 days the reaction mixture was concentrated, re-dissolved in CH2Cl2, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuum to obtain 1.48g (62%) of 1 and 1.10g (50.1%) of 2. 4.1.2.2 1-Ethyl-1H-indole-5-carbaldehyde (1) (0025) M.p.: 64-66°C (CH2Cl2/Hex). IR (KBr): 1703, 1605, 1307, 769cm-1. 1H NMR (200MHz, CDCl3): δ 1.49 (3H, t, J= 7.2), 4.22 (2H, m), 6.66 (1H, d, J=3.3); 7.22 (1H, d, J=3.3), 7.42 (1H, d, J=8.4), 7.78 (1H, dd, J=8.4 and 1.4), 8.15 (1H, d, J=1.4), 10.0 (1H, s). 13C NMR (50MHz, CDCl3): δ 15.4 (CH3), 41.2 (CH2), 103.4 (CH), 109.9 (CH), 121.6 (CH), 126.5 (CH), 128.4 (C), 128.5 (CH), 129.3 (C), 139.0 (C), 192.5 (CH).
With sodium hydroxide In tetrahydrofuran Reflux;
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
  • 2
  • [ 944893-74-7 ]
  • [ 1354970-03-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / 85 °C / Inert atmosphere 2.2: 12 h / 85 °C / Inert atmosphere
  • 3
  • [ 944893-74-7 ]
  • 1-ethyl-3,5-bis[(E)-2-(quinolin-8-yl)]-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / 85 °C / Inert atmosphere 2.2: 12 h / 85 °C / Inert atmosphere
  • 4
  • [ 944893-74-7 ]
  • [ 1354970-05-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / 85 °C / Inert atmosphere 2.2: 12 h / 85 °C / Inert atmosphere
  • 5
  • [ 944893-74-7 ]
  • [ 1354970-06-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / 85 °C / Inert atmosphere 2.2: 12 h / 85 °C / Inert atmosphere
  • 7
  • [ 944893-74-7 ]
  • [ 117507-84-3 ]
  • C32H30N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 20℃;
  • 8
  • [ 944893-74-7 ]
  • [ 117507-84-3 ]
  • [ 1620139-75-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0 °C
  • 9
  • [ 944893-74-7 ]
  • [ 155252-35-0 ]
  • C33H32N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 20℃;
  • 10
  • [ 944893-74-7 ]
  • [ 155252-35-0 ]
  • [ 1620139-76-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / ethanol / 20 °C 2: sodium tetrahydroborate / ethanol / 0 °C
  • 11
  • [ 944893-74-7 ]
  • [ 2840-44-0 ]
  • C21H18FNO [ No CAS ]
  • 16
  • [ 944893-74-7 ]
  • [ 2840-44-0 ]
  • (2E)-2-[(1-ethyl-1H-indol-5-yl)methylidene]-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; at 20℃; Sodium hydroxide (8 M, 0.6 mL) was added to a mixture of <strong>[2840-44-0]7-fluoro-1-tetralone</strong> (82 mg, 0.5 mmol) and N-ethyl-indole-5-carbaldehyde (85 mg, 0.5 mmol) in three (3) mL of EtOH and stirred at room temperature overnight. The resulting precipitate was collected via filtration, and washed with EtOH and water to yield Compound 8 as a fineyellow solid.?H NMR (400MHz, DMSO-d6): 1.37(t,J= 6.4 Hz, 3H), 2.91-2.95 (m, 2H),2.91-2.95 (m, 2H), 4.24 (q, J= 6.4 Hz, 2H), 6.52 (d, J= 3.2 Hz, 1H), 7.35 (d, J= 8.4,1.6 Hz, 1H), 7.37 (m, 3H), 7.56-7.58 (d, J 8.4 Hz, 1H), 7.63 (d, J 8.8, 2.4 Hz, 1H),7.82 (s, 1H), 7.95 (s, 1H). ESI(+)- MS m/z calc?d for C2,H,8FNO: 319.38; found: 321.3(M+2H), 640.8 (2M+2H)2.
  • 17
  • [ 944893-74-7 ]
  • [ 61240-20-8 ]
  • (Z)-1-ethyl-5-(3,4,5-trimethoxystyryl)-1H-indole [ No CAS ]
  • (E)-1-ethyl-5-(3,4,5-trimethoxystyryl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% Stage #1: triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 1h; Inert atmosphere; Stage #2: 1-ethyl-1H-indole-5-carbaldehyde In tetrahydrofuran; hexane at -40 - 20℃; for 24h; 10 4.1.2.12 (Z)-1-Ethyl-5-(3,4,5-trimethoxystyryl)-1H-indole (13) To a suspension of triphenyl(3,4,5-trimethoxybenzyl)phosphonium bromide (11, 1.67g, 3.19mmol) in dry THF (40mL), at-40°C in argon atmosphere, nBuLi (1.6M in hexane, 2.0mL, 3.2mmol) was added and stirred for 1h. A solution of 1-ethyl-1H-indole-5-carbaldehyde (1, 500mg, 2.89mmol) in dry THF (10mL) was slowly added at-40°C and progressively warmed to room temperature. After 24h, the reaction mixture was poured into ammonium chloride solution and extracted with CH2Cl2. The organic layers were washed to neutrality with brine, dried over anhydrous Na2SO4, filtered and evaporated to dryness. After chromatography on silica gel (Hex/EtOAc 85/15), 130mg (0.40mmol, 14%) of 13Z and 161mg (0.51mmol, 18%) of a mixture 13Z/13E were obtained. 4.1.2.13 (Z)-1-Ethyl-5-(3,4,5-trimethoxystyryl)-1H-indole (13) (0038) IR (film): 1685, 1579, 1127, 1007, 796, 722cm-1. 1H NMR (200MHz, CDCl3): δ 1.51 (3H, t, J=7.3), 3.62 (6H, s), 3.85 (3H, s), 4.18 (2H, c, J= 7.3), 6.41 (1H, d, J=3.1); 6.43 (1H, d, J=12.3), 6.57 (2H, s), 6.72 (1H, d, J=12.3), 7.08 (1H, d, J=3.1), 7.20 (2H, bs), 7.60 (1H, bs). 13C NMR (50MHz, CDCl3): δ 15.5 (CH3), 41.1 (CH2), 55.9 (2) (CH3), 60.9 (CH3), 103.3 (CH), 106.1 (2) (CH), 108.9 (CH), 121.7 (CH), 122.8 (CH), 127.4 (CH), 128.3 (C), 128.7 (C), 129.8 (CH), 131.4 (CH), 133.3 (C), 135.0 (C), 135.6 (C), 152.8 (2) (C). HRMS (C21H23NO3): calcd. 337.1678 (M+), 337.1699.
  • 18
  • [ 1196-69-6 ]
  • [ 75-03-6 ]
  • [ 944893-74-7 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 1H-indole-5-carboxaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 35℃; for 18h;
91% Stage #1: 1H-indole-5-carboxaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 35℃; for 18h; d.24.1 Step 1. Synthesis of 1-ethylindole-5-carbaldehyde. In a screw capped pressure tube 1H-indole-5- carboxaldehyde (338 mg, 2.3 mmol) was dissolved with 2.0 ml of anhydrous DMF then potassium carbonate (638 mg, 4.6 mmol) was added and the mixture kept under stirring for 10 minutes at rt. Iodoethane (503 mg, d = 1.94 g/ml, 344 m, 4.6 mmol) was then added. The reaction was thus heated to 35 °C and stirred for 18 hours. The crude mixture was diluted with DCM and washed three times with water. The organic layer was anhydrified through a phase separator and the solvent removed under reduced pressure. Purification by normal phase flash column chromatography (solvent A: CHX, solvent B: EtOAc - gradient: 0-5% solvent B) yielded title compound (363 mg, yield 91%). NMR (400 MHz, DMSO-de) 59.98 (s, 1H), 8.18 (t, J = 1.1 Hz, 1H), 7.71 - 7.62 (m, 2H), 7.57 (d, J = 3.2 Hz, 1H), 6.67 (dd, J = 3.2, 0.7 Hz, 1H), 4.27 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H). Rt1.94 min (generic method). ESI-MS for CiiHiiNO: calculated 173.1, found m/z 174.1 [M+H]+.
  • 19
  • [ 944893-74-7 ]
  • 6-chloro-3-(5-(1-ethyl-1H-indol-5-yl)-4,5-dihydro-1H-pyrazol-3-yl)-4-phenylquinolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / water; ethanol / 0.75 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrazine hydrate / ethanol / 0.75 h / 110 °C / Microwave irradiation
  • 20
  • [ 944893-74-7 ]
  • 4-(3-(6-chloro-2-oxo-4-phenyl-1,2-dihydroquinolin-3-yl)-5-(1-ethyl-1H-indol-5-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / water; ethanol / 0.75 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrazine hydrate / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: tetrahydrofuran / 0.75 h / 120 °C / Microwave irradiation
  • 21
  • [ 944893-74-7 ]
  • 3-(1-acetyl-5-(1-ethyl-1H-indol-5-yl)-4,5-dihydro-1H-pyrazol-3-yl)-6-chloro-4-phenylquinolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / water; ethanol / 0.75 h / 0 °C 1.2: 0 - 20 °C 2.1: hydrazine hydrate / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: tetrahydrofuran / 0.75 h / 165 °C / Microwave irradiation
  • 22
  • 3-acetyl-6-chloro-4-phenylquinolin-2-(1H)-one [ No CAS ]
  • [ 944893-74-7 ]
  • (E)-6-chloro-3-(3-(1-ethyl-1H-indol-5-yl)acryloyl)-4-phenylquinolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 3-acetyl-6-chloro-4-phenylquinolin-2-(1H)-one With potassium hydroxide In ethanol; water at 0℃; for 0.75h; Stage #2: 1-ethyl-1H-indole-5-carbaldehyde In ethanol; water at 0 - 20℃;
  • 23
  • [ 944893-74-7 ]
  • [ 196618-13-0 ]
  • (3R,4R,5S)-4-acetamido-5-(((1-ethyl-1H-indol-5-yl)methyl)amino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium cyanoborohydride / methanol / 6 h / 20 °C 2.1: sodium hydroxide; water / methanol / 20 °C / pH 14 2.2: pH 2-3
  • 25
  • [ 944893-74-7 ]
  • ±(3aS,3bR,11bR)-10-methoxy-2,3,3a,3b,4,5,6,11b-octahydro-1H-dipyrrolo[1,2-a:3',2'-c]quinoline [ No CAS ]
  • ±(3aR,3bR,11bR)-1-((1-ethyl-1H-indol-5-yl)methyl)-10-methoxy-2,3,3a,3b,4,5,6,11b-octahydro-1H-dipyrrolo[1,2-a:3',2'-c]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 6h; General procedure F: General procedure: (for the synthesis of compound A23-A36)To a solution of compound 7 (0.2 mmol) and aldehyde (0.4 mmol)in DCE was added NaBH(OAc)3. The mixture was stirred overnightat room temperature for 6 h and concentrated under vacuum. Theresidue was dissolved in ethyl acetate (20 mL), then washed withbrine (15 mL 3) and dried over Na2SO4 and concentrated. Theresidue was purified by column chromatography to afford theproduct.
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