Tag: M.W=200-300

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. 919103-45-0, name is 6-Iodoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

0.88 g (7.23 mmol) 4-N,N-dimethylaminopyridine and 44.6 mL (101.2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) 6-iodo-1,3-dihydro-indol-2-one in 125.0 mL N,N-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10 C. to the reaction mixture and stirred for 2 h at -10 C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL conc. hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50 C. in vacuo.

The synthetic route of 919103-45-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ZAHN, Stephan Karl; SINI, Patrizia; BISTER, Bojan; US2014/18405; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, 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 5332-26-3, Recommanded Product: 5332-26-3

Salt (n-Bu4N)2[2-B10H9SH] (0.50g, 0.79mmol), N-(bromomethyl)phthalimide (0.19g, 0.84mmol), and cesium carbonate (0.26g, 0.39mmol) were placed in a 25-ml round-bottom flask and dissolved in 4ml DMF. The solution was heated to 40C in an argon atmosphere for 2h. After cooling to room temperature, a precipitate was removed by filtration and the solvent was distilled off on a rotary evaporator, and the dry residue was resuspended in 15ml of distilled water and allowed to stand in an ultrasonic bath to form a flocculated suspension. The precipitate was filtered off and washed with distilled water (2×10ml) and ethyl acetate (3×5 ml). Yield: 94%. Anal. calc. for C41H87B10N3O2S (%): C, 61.99; H, 11.04; N, 5.29; S, 4.04. Found (%): C, 61.72; H, 11.12; N, 5.15; S, 3.90. (0013) 1H NMR (CD3CN, delta, ppm): 7.74 (m, 4H, Ph), 4.24 (s, 2H, SCH2), 3.11 (m, 8H, n-Bu4N+), 1.61 (m, 8H, n-Bu4N+), 1.35 (m, 8H, n-Bu4N+), 0.96 (t, 12H, n-Bu4N+), 0.60-2.10 (m, 9H, B10H9). (0014) 13C NMR (CD3CN, delta, ppm): 168.3 (CO), 134.8, 133.4, 123.6 (Ph), 59.3 (n-Bu4N+), 41.5 (SCH2), 24.4 (n-Bu4N+), 20.3 (n-Bu4N +), 13.8 (n-Bu4N +). (0015) 11B-{1H} NMR (CD3CN, delta, ppm): -0.1 (d, 1B), -2.6 (d, 1B), -16.6 (s, 1B), -24.9 (d, 4B), -27.6 (d, 2B), -28.8 (d, 1B). (0016) IR (CCl4): 3467, 3087, 3070, 3042, 3030, 2978, 2950, 2875, 2500, 2477, 1773, 1702, 1614, 1455, 1439, 1401, 1372, 1318, 1190, 1158, 1107, 1083, 1010, 987, 941, 875,790, 711, 644, 605, 520cm-1.

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-(Bromomethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kubasov; Turishev; Golubev; Bykov, A.Yu.; Zhizhin, K.Yu.; Kuznetsov; Inorganica Chimica Acta; vol. 507; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3783-77-5, A common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, molecular formula is C12H11NO3, 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.

To a cold slurry of 2-(3-oxobutyl)isoindoline-l,3-dione (2.12 g, 9.76 mmol) in MeOH (25 mL) at 0 C was added bromine (1.006 mL, 19.52 mmol). The reaction mixture was allowed to slowly warm to room temperature overnight. The reaction mixture was initially quenched with 10 M aq H2SO4 (15 mL). Once the intermediate methyl ether was no longer visible by LCMS, the reaction mixture was diluted with additional water (20 mL). The solid was collected, rinsed with water and air dried on the filter to afford 2-(4-bromo-3-oxobutyl)isoindoline-l,3-dione (2.13 g, 7.19 mmol, 73.7% yield) as a white solid. LC/MS (weak M+H): 295.9; LC retention time: 2.148 min (analytical HPLC Method N); NMR (400 MHz, CDCh): delta ppm 7.86 (dd, J=5.5, 3.1 Hz, 2H), 7.73 (dd, J=5.5, 3.1 Hz, 2H), 4.02 (t, J=7.2 Hz, 2H), 3.93 (s, 2H), 3.13 (t, J=7.2 Hz, 2H).

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WROBLESKI, Stephen T.; BROWN, Gregory D.; LIN, Shuqun; DUAN, Jingwu; LU, Zhonghui; DHAR, T.G. Murali; XIAO, Hai-Yun; TEBBEN, Andrew J.; (103 pag.)WO2016/149437; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 5332-26-3 as follows. Formula: C9H6BrNO2

Example 4 Diethyl phthalimidomethylphosphonate VII Triethyl phosphite (32 g, 192.59 mmol) was added to N-(bromomethyl)phthalimide III (46 g, 191.62 mmole) at room temperature and the reaction mixture was heated to 120 C. when vigorous reaction initiated by evolution of ethyl bromide gas. After 1 h at 120 C., the reaction mixture was allowed to cool down to room temperature and diluted with chloroform (250 ml). The mixture was washed with water (3*100 ml), brine (3*100 ml), dried over sodium sulfate and concentrated to furnish the phosphonate compound VII as a thick oil which is solidified on standing under vacuum; yield: 40 g; 70%. The crude material was carried over to the following step without further purification.

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HELVETICA INDUSTRIES (P) LIMITED; US2011/263870; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 3339-73-9 as follows. Formula: C11H9NO4

Oxalyl chloride (5.8 ml; 66.7 mmol) is added to Pht-beta-Ala-OH (9.96 g; 44.5 mmol) dissolved in dichloromethane (120 ml) and 3 drops of dimethylformamide (DMF). The mixture is stirred for 3 hours at ambient temperature. After elimination of the solvent, the white solid is taken up in a 1:1 mixture of anhydrous tetrahydrofuran and acetonitrile (200 ml) then 49 ml of a 2 M solution of (trimethylsilyl) diazomethane in hexane (97.9 mmol) are added dropwise at 0 C. The solvents are eliminated after one night of stirring at 0 C. The pale yellow solid is then dissolved in dichloromethane (60 ml) and 12 ml of aqueous hydrobromic acid (48%) is added dropwise at 0 C. The mixture is stirred until the temperature reaches 15 C. and 50 ml of a saturated solution of sodium bicarbonate is added. The organic phase is washed with salt water then dried over sodium sulphate. Crystallization from diethyl ether allows a white solid to be obtained (11.39 g; yield=86%). [00199] NMR 1H (DMSO D6, 100 MHz, delta): 7.83 (s, 4H); 4.36 (s, 2H, CH2Br); 3.8 (t, 2H, J=7.1 Hz, NCH2); 2.98 (t, 2H, J=6.9 Hz, CH2CO).

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6727269; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., SDS of cas: 552330-86-6

Step 1: 5-mercaptoisoindolin-1-one (0569) (0570) Sodium 2-methylbutan-2-olate (31.2 g, 282.96 mmol) was added to 5-bromoisoindolin-1-one (30 g, 141.48 mmol) and phenylmethanethiol (35.1 g, 282.96 mmol) in DMF (300 mL) under nitrogen. The resulting mixture was stirred at 100 C. for 12 hours. The reaction mixture was quenched with water (300 mL), extracted with EtOAc (3×300 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford 5-(benzylthio)isoindolin-1-one (6.00 g, 16.61%) as a yellow solid. The water layer was acidified with 2M HCl and the mixture was extracted with EtOAc (3×150 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness to afford 5-mercaptoisoindolin-1-one (15.00 g, 64.2%) as a solid. (0571) LC/MS: m/z=166 [M+H]+. 1H NMR (300 MHz, DMSO-d6) delta 4.32 (s, 2H), 5.88 (s, 1H), 7.37-7.40 (m, 1H), 7.49-7.54 (m, 2H), 8.45 (s, 1H).

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:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of isatin derivatives 1 (0.4 mmol), dienones 2 (0.6 mmol) and sarcosine (0.8 mmol) in CH3CN (10.0 mL) was stirred at 80 oC for 24 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1~3:1) to furnish the corresponding products 3.

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, 5-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiong-Li; Yang, Chao; Zhang, Wen-Hui; Zhou, Gen; Ma, Xi-Tao; Lin, Bing; Zhang, Min; Zhou, Ying; Feng, Ting-Ting; Tetrahedron Letters; vol. 57; 12; (2016); p. 1385 – 1389;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, 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.

Preparation 1 : ferf-Butyl 2-(6-bromo-1 -oxo-2,3-dihydro-1 H-isoindol-2-yl)acetate (1439) (1440) A suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (20 g, 94 mmol) and tert-butyl 2- bromoacetate (16.94 ml, 1 13 mmol) in DMF (320 mL) was cooled in an ice bath. Sodium hydride (4.53 g, 113 mmol) was added cautiously portionwise and the reaction was allowed to slowly warm to room temperature for 3 h. The reaction was quenched by the addition a saturated solution of NhUCI (650 mL) and the crude product was extracted with DCM (2 x 650 mL). The combined organic extracts were washed with water (4 x 650 mL) and brine (2 x 650 mL). The mixture was passed through a phase separator cartridge and the organic phase was concentrated under vacuum to give the crude product (40.1 g) as a dark orange semi-solid. 30g of the crude product were purified by chromatography (Si02, 2 x 220 g column, 0-50% EtOAc in isohexane) to afford the title compound as a yellow solid (19.5 g, 77%). LC-MS: [M-tBu+H]+ = 270/272.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

Step 1. Dimethyl (Phthalimidomethyl)phosphonate (ii). A mixture of N-(bromomethyl) phthalimide (i) (10.43 g, 43.46 mmol) and trimethyl phosphite (5.93 g, 47.80 mmol) was heated at reflux in xylene (20 mL) for 6 h. The reaction mixture was then cooled to room temperature and concentrated. Crystallization from CHCl3-hexane gave (ii) (7.60 g, 65%) as a white solid: 1H NMR (300 MHz, CDCl3) deltaH 3.84 (d, JH,P=10.8 Hz, 6H), 4.12 (d, J=11.4 Hz, 2H), 7.76 (m, 2H), 7.87 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Bromomethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; MethylGene, Inc.; US6472406; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, A new synthetic method of this compound is introduced below., name: tert-Butyl 5-bromoisoindoline-2-carboxylate

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5- bromo-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -78C under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -780C for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia / DCM gave 111 mg of 5-(4-hydroxy-1-methyl- piperidin-4-yl)-1 ,3-dihydro-isoindole-2-carboxyiic acid tert-butyl ester as a colourless oil.

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:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem