Tag: M.W=200-300

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H6BrNO

Sodium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran, 9.40 mL, 9.40 mmol) was added dropwise to a stirred suspension of 6-bromoindolin-2-one (preparation 1, 0.40 g, 1.89 mmol) in tetrahydrofuran (4 mL) at -78C. The mixture was stirred for 30 minutes, then 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (0.36 g, 1.89 mmol) was added and the mixture was warmed to room temperature. After stirring overnight, water was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated. Purification of the residue by reverse phase chromatography (0% CH3CN in H2O to 100% CH3CN in H2O) gave the title compound as a yellow oil (0.17 g, 31%). LRMS (m/z): 295/297 (M+1)+. 1H-NMR delta (DMSO-d6): 1.68-1.86 (m, 4H), 2.51-2.62 (m, 4H), 2.80-2.87 (s, 3H), 7.00 (s, 1H), 7.14 (d, J=6.0 Hz, 1H), 7.41 (d, J=6.0 Hz, 1H), 8.28 (brs, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 99365-40-9.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 118289-55-7, COA of Formula: C10H9Cl2NO

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

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Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 99365-40-9, Product Details of 99365-40-9

To a warm, stirred solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL toluene and 60 mL ethanol was added tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.9 mmol) followed by 2M aqueous sodium carbonate (50 mL, 100 mmol) and thiophene-2-boronic acid (4.38 g, 34.2 mmol) in three portions over 1.5 hours. The mixture was stirred at 100 C. in an oil bath for 12 hours. The mixture was then diluted with ethyl acetate (400 mL) and washed with saturated sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to give 2.53 g (42%) of 6-thiophen-2-yl-1,3-dihydro-indol-2-one a tan solid. 1H NMR (360 MHz, DMSO-d6) delta 10.42 (s, 1H, NH), 7.50 (dd, J=0.83 and 4.97 Hz, 1H, Ar-H), 7.43 (dd, J=0.89 and 3.52 Hz, 1H, Ar-H), 7.21 (s, 2H, Ar-H), 7.10 (dd, J=3.31 and 4.82 Hz, 1H, Ar-H), 7.01 (s, 1H, Ar-H), 3.47 (s, 2H, CH2CO). MS EI: 215 [M]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6689806; (2004); B1;,
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261732-38-1, name is tert-Butyl 5-bromoindoline-1-carboxylate, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of tert-Butyl 5-bromoindoline-1-carboxylate

Part 2. To a solution of N-Boc-5-bromoindoline (104 mg, 0.35 mmol) in 5 ml of anhydrous dioxane were added the boronic acid from Example 19 (100 mg, 0.39 mmol), cesium carbonate (228 mg, 0.7 mmol) and tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (10 mg, 0.01 mmol). The reaction flask was thoroughly flushed with argon, and tri-tert-butylphosphine (0.006 mL, 0.025 mmol) was added via syringe. The reaction was heated to 80 C. and stirred overnight. The reaction was then cooled to room temperature, diluted with 25 mL of diethyl ether, flushed through a pad of Celite and concentrated in vacuo to give a brown residue. This residue was subjected to flash column chromatography on silica gel using 25% ethyl acetate in hexane to give the desired biphenylamine (150 mg, 100%) as a light brown oil after drying. 1H NMR (CDCl3) delta: 1.02 (s, 9H); 1.22 (s, 9H); 3.10-3.15 (t, 2H); 4.02, (t, 2H); 7.25-8.14 (m, 7H).

The synthetic route of 261732-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US6534535; (2003); B1;,
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Application of 132898-96-5, The chemical industry reduces the impact on the environment during synthesis 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

Step 3: 3,3-Dimethyl-8-{[(2S)-2-(phenoxymethyl)-2,3-dihydro-1H-indol-1-yl]sulfonyl }-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one The title compound was prepared from 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride and (S)-2-phenoxymethyl-2,3-dihydro-1H-indole as a yellow foam according to a procedure similar to that of Example 12. NMR (400 Mz, DMSO-d6): consistent. MS: (ES-) m/z 500 [M-H].

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
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Related Products of 132898-96-5, A common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Bromoisoindoline-1,3-dione

To a solution of hydroxyproline tripeptide precursor (200 mgs, 0.359mmol) in 4 mL of DMF at room temperature was added 4-bromophthalimide(97 mgs, 0.430 mmol) and triphenyl phosphine (206 mgs, 0.789 mmol).Sonicate until dissolved and add DIAD (152 uL, 0.789 mmol). Stir at roomtemperature overnight. Remove solvent under reduced pressure and extractwith ethyl acetate and water. ‘Separate the layers and dry over MgSCu, filterand strip. Purify using silica gel chromatography eluting (10 -100% ethylacetate in hexane). Further purify on reverse phase HPLC (ACN/Water) toafford 102 as a white solid (98 mgs, 36%). 1H NMR (300 MHz, CDCls): 5 7.95(s, 1H), 7.88 (d, J=7.9 Hz, 1H), 7.71 (d, J= 7.7 Hz, 1H), 7.65 (s, 1H), 7.43 (s, 1H),6.03 (m, 1H), 5.37 (d, J= 15.5 1H), 5.31-5.07 (bs, 5H), 4.91 (m, 1H), 4.77 (m, 1H),4.23-4.03 (bs, 7H), 3.81 (t, J= 7.9Hz, 1H), 2.75 (m, 2H), 2.01 (m, 1H), 1.68-1,50(bs, 8H), 1.30 (q, J= 7.0 Hz, 6H), 1.10 (s, 1H), 0.99 (s, 9H). 31P NMR (300 MHz,CDCls): 8 22.92 (s, IP), 22.75 (s, IP). LC/MS: 766 (M++ 1).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2006/20276; (2006); A2;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 193354-13-1, name is 5-Iodoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Iodoindolin-2-one

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 65435-04-3 as follows. Safety of 5-(2-Chloroacetyl)indolin-2-one

A suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 ML pyridine at 80 to 90 C. for 3 hours then cooled to room temperature.. The precipitate was collected by vacuum filtration and washed with 20 ML ethanol.. The solid was dissolved in 90 ML 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours.. The mixture was cooled to room temperature and acidified to PH 2 with 0.5 N hydrochloric acid.. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.. After standing overnight the filtrate yielded 2 g of 5-carboxy-2-oxindole as a yellow solid.. The crude dark brown product was dissolved in hot methanol, the insoluble material removed by filtration and the filtrate concentrated to give 5.6 g of 5-carboxy-2-oxindole as a brown solid.. The combined yield was 97%.

According to the analysis of related databases, 65435-04-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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897957-06-1, name is 6-Bromo-1-methylindolin-2-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 897957-06-1

A solution of {S)-tert-hvXy 4-(l-amino-l-oxo-3-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 200 mg) and 6-bromo-l-methylindolin-2-one (87 mg) in acetonitrile (5 mL) was treated with potassium carbonate (107 mg) and purged with nitrogen. 1,1 bis(Di-tert- butylphosphino)ferrocene palladium dichloride (15 mg) was added and the reaction stirred under reflux under nitrogen for 4 h and then evaporated in vacuo. The residue was partitioned between water (40 mL) and ethyl acetate (40 mL). The aqueous was further extracted with ethyl acetate (40 mL) and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude product was purified by flash silica chromatography eluting with ethyl acetate. Pure fractions were evaporated to dryness to afford the sub-titled compound (45 mg).1H NMR (399.824 MHz, CDCl3) delta 7.54 (d, 2H), 7.32 – 7.28 (m, 3H), 7.22 (d, IH), 6.97 (s, IH), 6.88 – 6.80 (m, IH), 6.49 (d, IH), 5.27 (s, IH), 4.90 (s, IH), 4.80 (q, IH), 3.89 – 3.82 (m, IH), 3.69 – 3.62 (m, IH), 3.60 – 3.48 (m, 4H), 3.32 – 3.18 (m, 5H), 2.33 – 2.24 (m, IH), 1.92 – 1.76 (m, 2H), 1.35 (s, 9H).m/e (Multimode+) 437 [M+2H-BOC]+

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; METE, Antonio; MATHER, Andrew; MILLICHIP, Ian; WO2010/128324; (2010); A1;,
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