Tag: M.W=200-250

Huang, Shenlin published the artcileSynthesis and biological study of 2-amino-4-aryl-5-chloropyrimidine analogues as inhibitors of VEGFR-2 and cyclin dependent kinase 1 (CDK1), Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(8), 2179-2183, database is CAplus and MEDLINE.

The series of 2-amino-4-aryl-5-chloropyrimidines, e.g., I, was discovered to be potent for both VEGFR-2 and CDK1. Described here are the chem. for analog synthesis, SAR study, and its kinase selectivity profiling. The full rat PK data and in vivo efficacy study are also included.

Bioorganic & Medicinal Chemistry Letters published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Gu, Lijun published the artcileMicrowave-assisted synthesis of indole-2-carboxylic acid esters in ionic liquid, Computed Properties of 20538-12-9, the publication is Journal of the Brazilian Chemical Society (2011), 22(11), 2036-2039, database is CAplus.

An improved procedure for the synthesis of indole-2-carboxylic acid esters, e.g. Et 1-methoxy-1H-indole-2-carboxylate, in excellent yields has been achieved by the condensation of 2-halo aryl aldehydes or ketones and Et isocyanoacetate using ionic liquid under controlled microwave irradiation (100 W) at 50 掳C. This method offers a number of advantages in terms of methodol., high-product yield, short period of conversion, mild reaction conditions and easy workup.

Journal of the Brazilian Chemical Society published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Computed Properties of 20538-12-9.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zischler, Johannes published the artcileAlcohol-Enhanced Cu-Mediated Radiofluorination, COA of Formula: C14H18BNO2, the publication is Chemistry – A European Journal (2017), 23(14), 3251-3256, database is CAplus and MEDLINE.

The potential of many ¹⁸F-labeled (hetero)aromatics for applications in positron emission tomog. remains underexplored because convenient procedures for their radiosynthesis are lacking. Consequently, simple methods to prepare radiofluorinated (hetero)arenes are highly sought after. Herein, we report the beneficial effect of primary and secondary alcs. on Cu-mediated ¹⁸F-labeling. This observation contradicts the assumption that such alcs. are inappropriate solvents for aromatic fluorination. Therefore, we developed a protocol for rapid radiolabeling of an extraordinarily broad scope of boronic and stannyl substrates under general reaction conditions. Notably, radiofluorinated indoles, phenols, and anilines were synthesized directly from the corresponding unprotected precursors. Furthermore, the novel method enabled the preparation of radiofluorinated tryptophans, [¹⁸F]F-DPA, [¹⁸F]DAA1106, 6-[¹⁸F]FDA, and 6-[¹⁸F]FDOPA.

Chemistry – A European Journal published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C9H16BNO2, COA of Formula: C14H18BNO2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Majima, Riko published the artcileSynthetic experiments in the indole group. VII. Nitration and bromination of β-indolecarboxylic ester and a new synthesis of the dye of the purple of antiquity, Computed Properties of 10242-03-2, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1930), 2237-45, database is CAplus.

cf. C. A. 20, 758. A repetition of the work of Oddo and Sessa (C. A. 5, 2638) not only confirmed the earlier observation that, contrary to the statements of O. and S., Et β-indolecarboxylate (I) is formed by the action of ClCO₂Et on indolylmagnesium iodide but also showed that di-Et N, β-indoledicarboxylate (II) is formed at the same time; to obtain II in good yield it is well to use 2 mols. ClCO₂Et per mol. of indole. Addition of concentrated HNO₃ to I in cold AcOH gives chiefly Et 6-nitroindole-3-carboxylate (III), saponified by KOH to the free and (IV) which with hot quinoline gives 6-nitroindole (V). The position of the NO₂ group was established by oxidation of the salt of IV with aqueous KMnO₄ to 2,4-H₂N(O₂N)C₆H₃-CO₂H. With HCl and SnCl₂ in AcOH III readily yields the 3-amino ester (VI). V similarly gives the amorphous and very unstable 6-aminoindole (VII). I is readily brominated in AcOH, giving chiefly either Et 6-bromoindole-3-carboxylate (VIII) or the 5,6-di-Br ester (IX), depending on the conditions. The free di-Br acid (X) can be further converted into 5,6-dibromoindole (XI). X with CrO₃ in AcOH gives a red 5,6-dibromoisatin (XII), m. above 290°, which on distillation with KOH yields a Br₂C₆H₃NH₂, m. 79-80° (of the known Br₂C₆H₃NH₂, the 3,4-compound, m. 80.4°, comes closest in its properties to the one obtained from XII). XII on further oxidation with CrO₃ in AcOH gives a dibromoisatoic acid (XIII) which with concentrated HCl yields 4,5,2-Br₂(H₂N)C₆H₂CO₂H, m. 227-8°. In the same way VIII gave 6-bromoisatin (XIV), different from Borsche and Jacobs’ synthetic 5-Br compound With 03 in alk. solution, VIII readily gives 6,6′-dibromoindigo (XV), thus further confirming the structure of VIII. II (1.1 g. from 3 g. indole through the Mg compound with 2 mols. ClCO₂Et), less soluble in alc. than I, m. 102-3°. The yield of I has been increased to over 78% by slowly adding 11 g. ClCO₂Et to the Mg derivative from 11 g. indole in cold Et₂O. III, light yellowish needles, m. 198-9°. IV, yellow, becomes opaque at 227°, decomposes around 275-8°; its alkali salts dissolve in H₂O with orange-red color. V, yellow, m. 139-40.5°. VI, m. 149-50°; HCl salt; chloroplatinate. β-Indolealdehyde in AcOH with HNO₃ (d. 1.4) gives an addition product, C₉H₇ON.HNO₃, decomposes 94°; with excess of HNO₃ on the H₂O bath is obtained a nitro-β-indolealdehyde, light yellow, m. around 290° (decomposition), turns brownish in the air. VIII, m. 134-7°; free acid, m. 212°. IX (85% from 2 g. I and 4 g. Br), m. 223-5°. X, m. 255-7°; if, in the saponification of IX, the boiling with excess of ale. KOH is continued 10 hrs. the product is XI, m. 154°. XII, m. 290°, shows the indopbenin reaction, gives with dilute NaOH a dark violet precipitate which redissolves with yellow color on heating and acids reppt. the original XII. XIV, orange-red, m. 256-8°. 5,5′,6,6′-Tetrabrornoindigo, is obtained from IX with O₃; it dyes silk in somewhat less reddish shades than XV, the chief constituent of the purple of the ancients.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 10242-03-2. 10242-03-2 belongs to indole-building-block, auxiliary class Indole,Nitro Compound,Carboxylic acid,Indole, name is 6-Nitro-1H-indole-3-carboxylic acid, and the molecular formula is C9H6N2O4, Computed Properties of 10242-03-2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Jiang, Fanwei published the artcileSynthesis of substituted indole-3-carboxylic acid derivatives, Category: indole-building-block, the publication is Huaxue Tongbao (2015), 78(4), 378-380, database is CAplus.

Indole-3-carboxylic acid was a kind of important organic intermediate, which could be widely used in the synthesis of medicine and pesticide. Substituted 2-nitro-β-dimethylamino styrene was obtained from the reaction of substituted 2-nitrotoluene and N,N-dimethylformamide di-Me acetal in N,N-dimethylformamide, which was further reacted with iron and acetic acid to give substituted indoles. Five substituted indole-3-carboxylic acids were synthesized from substituted indoles and trifluoroacetic anhydride. The reported synthesis had the advantages of simple post treatment, mild conditions and higher yields.

Huaxue Tongbao published new progress about 10242-03-2. 10242-03-2 belongs to indole-building-block, auxiliary class Indole,Nitro Compound,Carboxylic acid,Indole, name is 6-Nitro-1H-indole-3-carboxylic acid, and the molecular formula is C9H6N2O4, Category: indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles