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Chemistry
Heterocyclic Building Blocks
Indolines
4-Methoxy-1-methylindolin-2-one
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Indolines
Amides Ethers

[ CAS No. 7699-21-0 ]

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 7699-21-0
Chemical Structure| 7699-21-0
Chemical Structure| 7699-21-0
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Quality Control of [ 7699-21-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 7699-21-0 ]

Product Details of [ 7699-21-0 ]

CAS No. :7699-21-0 MDL No. :MFCD13178646
Formula : C10H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QRGVWBMIQHILSZ-UHFFFAOYSA-N
M.W :177.20 Pubchem ID :12713031
Synonyms :

Safety of [ 7699-21-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7699-21-0 ]

* 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 [ 7699-21-0 ]

[ 7699-21-0 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 7699-17-4 ]
  • [ 74-88-4 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate Behandeln des Reaktionsprodukts mit wss.Natronlauge;
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In tetrahydrofuran at 20℃; for 21h; 8.i 4-Methoxy-1,3-dihydro-2H-indol-2-one (801 mg) was dissolved in tetrahydrofuran (40 mL), iodomethane (0.46 mL), tetrabutylammonium iodide (101 mg) and finely triturated potassium hydroxide (420 mg) were added, and the mixture was stirred at room temperature for 21 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=95:5→33:67) to give the title compound (458 mg) as a pale-yellow powder. 1H-NMR (CDCl3) δ: 3.20 (3H, s), 3.45 (2H, s), 3.86 (3H, s), 6.50 (1H, d, J = 7.7 Hz), 6.62 (1H, d, J = 8.3 Hz), 7.20-7.30 (1H, m)
Reference： [1]Cook et al. [Journal of the Chemical Society, 1952, p. 3904,3909]
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2103620, 2009, A1 Location in patent: Page/Page column 36
  • 2
  • [ 21744-84-3 ]
  • [ 7699-21-0 ]
  • [ 7699-23-2 ]
Reference： [1]Journal of the Chemical Society,1952,p. 3904,3909
[2]Journal of the Chemical Society,1952,p. 3904,3909
  • 3
  • [ 7699-21-0 ]
  • [ 7569-83-7 ]
  • [ 7556-35-6 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; diethyl ether
Reference： [1]Cook et al. [Journal of the Chemical Society, 1952, p. 3904,3909]
  • 4
  • [ 7699-21-0 ]
  • [ 20870-81-9 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride at 120℃;
With hydrogen bromide Heating;
With hydrogen bromide In water for 60h; Reflux; 8.ii A mixture of 4-methoxy-1-methyl-1,3-dihydro-2H-indol-2-one (600 mg) and 48% hydrobromic acid (6 mL) was stirred with heating under reflux for 60 hr. Water was added to the reaction mixture, and the mixture was extracted with a mixed solvent of ethyl acetate/tetrahydrofuran. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was collected by filtration to give the title compound (515 mg) as an orange powder. 1H-NMR (CDCl3) δ: 3.20 (3H, s), 3.48 (2H, s), 5.21 (1H, s), 6.46 (1H, d, J = 8.0 Hz), 6.53 (1H, d, J = 8.0 Hz), 7.17 (1H, t, J = 8.0 Hz)
Reference： [1]Loudon; Ogg [Journal of the Chemical Society, 1955, p. 739,743]
[2]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
[3]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2103620, 2009, A1 Location in patent: Page/Page column 36
  • 5
  • [ 77747-62-7 ]
  • [ 7699-21-0 ]
  • [ 7699-23-2 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride at 220℃; Erwaermen des Reaktionsprodukts mit Methyljodid und Kaliumcarbonat in Aceton;
Reference： [1]Loudon; Ogg [Journal of the Chemical Society, 1955, p. 739,743]
  • 6
  • [ 7699-21-0 ]
  • [ 81963-72-6 ]
YieldReaction ConditionsOperation in experiment
With lead dioxide In benzene for 0.5h; Heating; Yield given;
Reference： [1]Bruni, P.; Cardellini, L.; Cardillo, B.; Tosi, G. [Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 211 - 213]
  • 7
  • [ 65836-81-9 ]
  • [ 7703-91-5 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
1: 66% 2: 6% With sodium hydrogencarbonate In water; acetonitrile Irradiation;
Reference： [1]Hamada; Okuno; Ohmori; et al. [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 1, p. 128 - 136]
  • 8
  • C10H11LiNO3(1-)*Li(1+) [ No CAS ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride Yield given;
Reference： [1]Rewcastle, Gordon W.; Denny, William A. [Heterocycles, 1994, vol. 37, # 2, p. 701 - 708]
  • 9
  • [ 7699-21-0 ]
  • [ 131071-36-8 ]
YieldReaction ConditionsOperation in experiment
92% With tetraphosphorus decasulfide; sodium carbonate In tetrahydrofuran Ambient temperature;
80% 4 Stage A: 1-Methyl-4-Methoxy-2-Indolinethione Stage A: 1-Methyl-4-Methoxy-2-Indolinethione Using the procedure described in Example 3, but replacing 5-methoxy-1-methyl-2-indolinone by 4-methoxy-1-methyl-2-indolinone, the expected product is obtained. Yield: 80%. Melting point: 144°-145° C. Analysis: Calculated: C: 62.15, H: 5.74, N: 7.25, S: 16.59. Found: C: 61.79, H: 5.59, N: 7.10, S: 16.75.
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
[2]Current Patent Assignee: ADIR - US5030646, 1991, A
  • 10
  • [ 124-38-9 ]
  • [ 156267-10-6 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium Multistep reaction;
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
YieldReaction ConditionsOperation in experiment
N-Methyl-N-chloracetyl-o-anisidin, 1) AlCl3, 2) Dimethylsulfat, Na-Ethylat;
  • 12
  • [ 7699-21-0 ]
  • [ 156136-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 48percent HBr in glacial AcOH / Heating 2: pyridine / 20 °C
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
  • 13
  • [ 7699-21-0 ]
  • [ 156136-75-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 48percent HBr in glacial AcOH / Heating 2: pyridine / 20 °C 3: 94 percent / Na2CO3, P2S5 / tetrahydrofuran / Ambient temperature
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
  • 14
  • [ 7699-21-0 ]
  • [ 1026338-22-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / Na2CO3, P2S5 / tetrahydrofuran / Ambient temperature 2: 1.) NaH / 1.) THF, 2.) THF
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
  • 15
  • [ 7699-21-0 ]
  • [ 1028267-53-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 48percent HBr in glacial AcOH / Heating 2: pyridine / 20 °C 3: 94 percent / Na2CO3, P2S5 / tetrahydrofuran / Ambient temperature 4: 1.) NaH / 1.) THF, 2.) THF
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
  • 16
  • [ 7699-21-0 ]
  • C34H30N4O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 92 percent / Na2CO3, P2S5 / tetrahydrofuran / Ambient temperature 2: 1.) NaH / 1.) THF, 2.) THF 3: air / methanol / 20 °C
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
  • 17
  • [ 7699-21-0 ]
  • 2,2'-dithiobis [N-phenyl 4-acetoxy-1-methylindolyl-3-carboxamide] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 48percent HBr in glacial AcOH / Heating 2: pyridine / 20 °C 3: 94 percent / Na2CO3, P2S5 / tetrahydrofuran / Ambient temperature 4: 1.) NaH / 1.) THF, 2.) THF 5: air / methanol / 20 °C
Reference： [1]Rewcastle; Palmer; Dobrusin; Fry; Kraker; Denny [Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2033 - 2042]
  • 18
  • [ 156267-10-6 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi 2: 0.1M aq. HCl
Reference： [1]Rewcastle, Gordon W.; Denny, William A. [Heterocycles, 1994, vol. 37, # 2, p. 701 - 708]
  • 19
  • [ 156267-25-3 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaBH4 2: 1.) n-BuLi 3: 0.1M aq. HCl
Reference： [1]Rewcastle, Gordon W.; Denny, William A. [Heterocycles, 1994, vol. 37, # 2, p. 701 - 708]
  • 20
  • [ 19500-02-8 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: NaBH4 3: 1.) n-BuLi 4: 0.1M aq. HCl
Reference： [1]Rewcastle, Gordon W.; Denny, William A. [Heterocycles, 1994, vol. 37, # 2, p. 701 - 708]
  • 21
  • [ 14318-66-2 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / NaHCO3 / CH2Cl2; H2O / Ambient temperature 2: 6 percent / NaHCO3 / acetonitrile; H2O / Irradiation
Reference： [1]Hamada; Okuno; Ohmori; et al. [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 1, p. 128 - 136]
  • 22
  • [ 10541-78-3 ]
  • [ 7699-21-0 ]
Reference： [1]Journal of the Chemical Society,1955,p. 739,743
  • 23
  • [ 20876-28-2 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium; acetic acid / Hydrogenation 2: methanol. sodium methylate / Behandeln des Reaktionsprodukts mit wss.Natronlauge
Reference： [1]Cook et al. [Journal of the Chemical Society, 1952, p. 3904,3909]
  • 24
  • [ 20876-27-1 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aqueous HCl 2: palladium; acetic acid / Hydrogenation 3: methanol. sodium methylate / Behandeln des Reaktionsprodukts mit wss.Natronlauge
Reference： [1]Cook et al. [Journal of the Chemical Society, 1952, p. 3904,3909]
  • 25
  • [ 64208-72-6 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aqueous ethanol 2: aqueous HCl 3: palladium; acetic acid / Hydrogenation 4: methanol. sodium methylate / Behandeln des Reaktionsprodukts mit wss.Natronlauge
Reference： [1]Cook et al. [Journal of the Chemical Society, 1952, p. 3904,3909]
  • 26
  • [ 7699-21-0 ]
  • [ 1255957-66-4 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide In methanol; chloroform at -10℃; for 0.666667h; 36.c To a solution of 4-methoxy-1-methyl-1 3-dιhydro-ιndol-2-one (440 mg, 2 483 mmol) in chloroform (25 ml) was added methanol (25 00 ml) The reaction was put at -10 °C and N-bromosucαnimide (442 mg, 2 483 mmol) was added in three portions over a 30 mm interval and the reaction was then stirred for 10 minutes The reaction was then diluted with dichloromethane saturated aqueous sodium bicarbonate, and saturated aqueous sodium thiosulfate and the layers were separated The aqueous layer was extracted two additional times with dichloromehtane and the organic layers were combined, dried over anhydrous sodium sulfate filtered, and concentrated The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane 0 to 60%) to afford 5-bromo-4- methoxy-1-methyl-1 ,3-dιhydro-mdol-2-one, MS (ES+) m/z 255 8 (M+H)4
Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2010/130794, 2010, A1 Location in patent: Page/Page column 91
  • 27
  • [ 7556-35-6 ]
  • [ 7699-21-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-methoxy-1-methyl-1H-indole With water; bromine; potassium bromide In <i>tert</i>-butyl alcohol for 0.5h; Stage #2: With hydrogen; acetic acid In ethanol for 18h; 36.b To a solution of potassium bromide (3986 mg, 33 5 mmol) in water (26.5 ml) was added bromine (0 863 ml 16.75 mmol) A separate flask containing 4-methoxy-1 -methyl- 1 H- indole (900 mg, 5 58 mmol) was charged with t-butano. (20 00 ml) and water (20 0 ml) To this flask was added 22.5 mL of bromine solution dropwise The mixture was permitted to stir for approximately 30 minutes and then was neutralized wrth saturated aqueous sodium bicarbonate and quenched with saturated aqueous sodium thiosulfate. The reaction was then diluted with dichloromethane and saturated aqueous sodium bicarbonate and the layers were separated The aqueous layer was extracted two additional times with dichloromethane and the organic layers were combined dried over anhydrous sodium sulfate, filtered, and concentrated The resulting residue was dissolved in 50 mt_ EtOH and 5 mL of AcOH The solution was then charged with 10% palladium on carbon (1 2 g, 1 13 mrnol) The atmosphere over the reaction mixture was evacuated and the reaction was placed under an atmosphere of hydrogen gas via a balloon The reaction was stirred for 18 hours The reaction mixture was then filtered through a plug of Celite and the filtrate was then concentrated to approximately 25% of its original volume The reaction was then diluted with dichloromethane and saturated aqueous sodium bicarbonate and the layers were separated The aqueous layer was extracted two additional times with dichloromethane and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated The resulting residue was punfied by silica gel flash chromatography (ethyl acetate-heptane, O to 60%) to afford 4-methoxy-1-methyl-1 3-dιhydro-tndol-2-one MS (ES+) m/z 178 0 (M+H)*
Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2010/130794, 2010, A1 Location in patent: Page/Page column 90; 91

Tags: 7699-21-0 synthesis path| 7699-21-0 SDS| 7699-21-0 COA| 7699-21-0 purity| 7699-21-0 application| 7699-21-0 NMR| 7699-21-0 COA| 7699-21-0 structure

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