Month: March 2022

81779-27-3, 4-Hydroxy-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,81779-27-3

1: 0.40 g (1 mmol) of compound 0.66 g (1.1 mmol) of compound 2 was dissolved in 20 mL of methanol, and two drops of piperidine were added dropwise.As a catalyst, a reflux reaction was carried out under a nitrogen atmosphere, and the reaction was completed overnight, and the reaction was completed. Pass the crude product through column chromatographyThe developing agent of CH2Cl2/CH3OH=70:1 was separated and purified to obtain compound 3, and subjected to nuclear magnetic resonance spectroscopy.Structure (see Figure 1).

The synthetic route of 81779-27-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; University of Jinan; Lin Weiying; Wang Weishan; Liu Yong; Niu Jie; (10 pag.)CN108640902; (2018); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

1008-07-7, 7-Chloro-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 7-chloro-1H-indole-3-carboxaldehyde36 (3.6 g, 20 mmol),hydroxylamine hydrochloride (1.40 g, 20 mmol), sodium acetate (1.60 g,20 mmol), glacial acetic acid (63 g, 60 mL) and acetic anhydride (2.2 g,2 mL) was placed in a round bottomed flask and heated under reflux for 4 h. Then the reaction mixture was cooled and poured into ice water. The resulting precipitate was filtered, washed with water, dried and recrystallised from methanol to give the pure product 7-chloro-1H-indole-3-carbonitrile (3.1 g, 88% yield): m.p. 180-182 C. 1H NMR(DMSO-d6, 400 MHz) delta 7.19-7.35 (m, 2H), 7.58-7.64 (m, 1H), 8.32 (d,J = 5.0 Hz, 1H), 12.61 (s, 1H). 13C NMR (DMSO-d6, 100 MHz) delta 113.5,115.7, 118.3, 119.6, 120.1, 122.2, 123.4, 127.9, 137.4. IR (KBr) numax/cm-1 3272, 3124, 2240, 1583, 1441, 1352, 1300, 1211., 1008-07-7

1008-07-7 7-Chloro-1H-indole-3-carbaldehyde 643958, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Wang, Hongshe; Zhao, Weixing; Journal of Chemical Research; vol. 39; 6; (2015); p. 321 – 323;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

32588-36-6, Indole-2-acetic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 11 (1.2 g, 6.34 mmol) and KOH (6.7, 0.12 mol) taken in a reaction flask was dissolved in 150 mL of EtOH, to this stirred reaction mixture was slowly added 80 % N2H4 (5 mL) at rt. Later the reaction mixture was refluxed for 5 h then the reaction mixture was heated to 150 C and was maintained at the same temperature for 45 min. Then, the reaction mixture was cooled to 0C and acidified (pH=2-3) with 5 % aq HCl. The organic layer was separated and the aqueous layer was extracted with Et2O (3 × 50mL). The combined organic layers were washed with brain, and dried over MgSO4. The solvent was removed under reduced pressure and the crude product 12 was dissolved in a mixture of MeOH (13 mL) and benzene (48 mL). To this solution, 4mL of 8 mmol of TMSCHN2 was added and the resulting reaction mixture was stirred for 30min at rt. Then all the volatile materials were removed under reduced pressure, later the solid residue was dissolved in CH2Cl2 and washed with aq Na2CO3. The organic fraction was dried (MgSO4) and the solvent removed under reduced pressure and the crude product was purified by flash column chromatography (EtOAc : Hexane=3 : 2) to yield 13 (75 %). mp 70.3-71.4C (lit [25]. 68.0-71.0C); 1H NMR (500 MHz, CDCl3): delta 8.79 (1H, br-s, N-H), 7.54-7.12 (4H, m, Ar-H), 6.34 (1H, s, Ar-H), 3.82 (2H, s, CH2), 3.74 (3H, s, CH3); 13C NMR (125.77 MHz, CDCl3): delta 171.0, 136.3, 130.3, 128.1, 121.7, 120.1, 119.7, 110.8, 101.8, 52.3, 33.7. MS (FAB) m/z 189 (M+H)., 32588-36-6

32588-36-6 Indole-2-acetic acid 4371752, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Mori, Ryota; Kato, Asako; Komenoi, Kousuke; Kurasaki, Haruaki; Iijima, Touru; Kawagoshi, Masashi; Kiran; Takeda, Sho; Sakai, Norio; Konakahara, Takeo; European Journal of Medicinal Chemistry; vol. 82; (2014); p. 16 – 35;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate-69: tert-Butyl lH-indol-5-ylcarbamate To a stirred solution lH-indol-5 -amine (0.5 g, 3.78 mmol) in dichloromethane (10 mL), triethylamine (0.95g, 9.4 mmol) and di-tert-butyl dicarbonate (0.908 g, 4.166 mmol) were added at 0C. The reaction contents were stirred at room temperature for 4 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give tert-butyl lH-indol-5-ylcarbamate (0.380 g, 43%); MS: 233.5 (M+l).

5192-03-0, As the paragraph descriping shows that 5192-03-0 is playing an increasingly important role.

Reference：
Patent; LUPIN LIMITED; THOTAPALLY, Rajesh; KACHI, Onkar, Gangaram; RODGE, Atish, Harishchandra; PATHAK, Ashok, Bhau; KARDILE, Bhavana, Shrirang; SINDKHEDKAR, Milind, Dattatraya; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/69917; (2012); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

165250-69-1, 4-Methyl-5-nitro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a cooled solution (ice-water bath) of 4-methyl-5-nitroindole (1.76 g, 10 mmol) in DMF (30 mL) was added KOH pellets (0.78 g, 14 mmol). The cooling bath was removed, and the mixture was stirred at rt for 10 min. Iodine (2.79 g, 11 mmol) was added, and the stirring was continued for 5 h at room temperature. To this mixture was added potassium carbonate (3.17 g, 23 mmol) and methyl iodide (3.1 mL, 50 mmol), and stirring was continued at room temperature for 16 h. The mixture was diluted with water (150 mL), and treated with solid NaHSO3 with stirring until all excess iodine was quenched. The crude product was collected by filtration, washed with plenty of water, and dried.

165250-69-1, The synthetic route of 165250-69-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER INC.; Schnute, Mark Edward; Wennerstal, Goeran Mattias; Blinn, James Robert; Kaila, Neelu; Kiefer, JR., James Richard; Mente, Scot Richard; Kurumbail, Ravi G.; Meyers, Marvin Jay; Thorarensen, Atli; Xing, Li; Zapf, Christoph Wolfgang; Zamaratski, Edouard; Flick, Andrew Christopher; Jones, Peter; (77 pag.)US2016/46597; (2016); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

1065181-58-9, Ethyl 5-bromo-1H-indole-7-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 72:(racem/cJ-Ethyl 5-bromo-3-(2,2-dimethyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7- carboxylate.2,2-Dimethyltetrahydro-4H-thiopyran-4-one (0.675 g, 4.68 mmol) was placed in a dried flask fitted up with an addition funnel, a septum and an argon inlet, and dissolved in dry DCM (15 mL), cooled to 0 0C, stirred, and then trimethylsilyl trifluoromethanesulfonate (1.692 mL, 9.36 mmol) was added dropwise through the addition funnel over 10 minutes. DCM (5 mL) was used to wash the addition funnel walls. To this mixture was added dropwise ethyl 5-bromo-1 H-indole-7- carboxylate (1.341 g, 5 mmol) in DCM (15 mL) over 2 hours. Then triethylsilane (2.98 mL, 18.73 mmol) was added in one portion. The mixture was stirred 2 h at 0 0C, and left stirring at 23 0C overnight. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture extracted with DCM to give 2.1 15 g of the title compound. LC/MS: m/z 398.0 (M+H), Rt 1.49 min., 1065181-58-9

The synthetic route of 1065181-58-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/118724; (2008); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32588-36-6,Indole-2-acetic acid,as a common compound, the synthetic route is as follows.

To a solution of compound 7 (100mg, 0.25 mmol)and 2-(1H-indol-2-yl)acetic acid (44 mg, 0.25 mmol) in 5 mlDMF was added HOAT (68 mg, 0.50 mmol), EDCI (78 mg,0.50 mmol) and DIPEA (129 mg, 1 mmol). The mixture wasstirred at 60 C. overnight, LCMS monitored the reaction tocompletion. The target compound 8 (80 mg, 766%) wasobtained as a yellow solid following extraction with EA andfiltration through silica gel.

32588-36-6, As the paragraph descriping shows that 32588-36-6 is playing an increasingly important role.

Reference：
Patent; Acetylon Pharmaceuticals, Inc.; Jones, Simon Stewart; Yang, Min; Tamang, David Lee; US2015/105384; (2015); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

39689-58-2, 2-(1H-Indol-6-yl)acetic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,39689-58-2

To a solution of the compound [4-5] obtained in the process (5) (497 mg) in N,N-dimethylformamide (10 mL) were added potassium carbonate (511 mg) and methyl iodide (0.12mL) at 0C, and then the reaction mixture was stirred at room temperature for 13 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (512 mg) as a white solid. 1H-NMR (400MHz, CD3 OD) delta: 8.25-8.00 (1H,br), 7.59 (1H,d, J = 8.1 Hz), 7.33 (1H,d, J = 0.7 Hz), 7.19 (1H,t, J = 2.8 Hz), 7.04 (1H, dd, J = 8.1, 1.2 Hz), 6.53 (1H, s), 3.73 (2H, s), 3.69 (3H, s).

39689-58-2 2-(1H-Indol-6-yl)acetic acid 14882503, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

23872-36-8, 4-Chloro-1H-indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Preparation of 4-Chloro-1-dimethylcarbamoylmethyl-1H-indole-3-carboxylic acid 2-chloro-N,N-dimethylacetamide (0.19 ml; 1.84 mmol; 1.20 eq.) was added to a solution of 4-Chloro-1H-indole-3-carboxylic acid (300.00 mg; 1.53 mmol; 1.00 eq.) and barium hydroxide octahydrate (967.67 mg; 3.07 mmol; 2.00 eq.) in DMF (15.63 ml; 202.65 mmol; 132.13 eq.) at 50° C. The reaction mixture was stirred overnight. The reaction mixture was diluted with DMSO (1 ml) and water (1 ml) then submitted to MPLC purification (Yamazen, Interchim 100 g polymeric Reverse Phase column, basic buffer) to afford the desired product 4-Chloro-1-dimethylcarbamoylmethyl-1H-indole-3-carboxylic acid (426.00 mg; 1.52 mmol) as a white solid. 1H NMR (400 muMHz, MeOD) delta 7.42 (s, 1H), 6.89-6.79 (m, 1H), 6.78-6.64 (m, 2H), 4.73 (s, 2H), 2.73 (s, 3H), 2.57-2.49 (m, 4H) ppm; [M+H]+ 281.1. LC-MS (254 nm) tR=3.47 min; HPLC (254 nm) Purity: >99percent; tR=2.68 min.

23872-36-8, As the paragraph descriping shows that 23872-36-8 is playing an increasingly important role.

Reference：
Patent; Merck Patent GmbH; KARRA, Srinivasa R.; (153 pag.)US2016/168090; (2016); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

170147-29-2, tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of scheme 6-6 compound S2 (2 g, 6.19 mmol) in MeCN (40 mL) at 0 C was added chlorosulfonyl isocyanate dropwise (0.57 mL, 6.50 mol). The reaction was stirred at room temperature overnight and then acetone (40 mL) and H20 (5 mL) was added followed by dropwise addition of 10% aq.KOH solution (2 mL). The mixture was stirred at room temperature for 30 mm and extracted with ethyl acetate (50 mL x 2). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was further washed with EtOAc to give the title compound (1.7 g, 75% yield) as a white solid. LC/MS (ESI) m/z: 311 (M-56+H) +, 170147-29-2

170147-29-2 tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate 10663688, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (358 pag.)WO2017/35411; (2017); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles