Category: 112279-60-4

Application of 112279-60-4, 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. 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A degassed solution of ethyl 3-(nonafluorobutane-l-sulfonyloxy)-furo[3,2- c]pyridine-2-carboxylate (500 mg, 1.02 mmol), 4-bromo-2,5-difluoroaniline (277 mg, 1.33 mmol), Pd2dba3 (47 mg, 0.05 mmol), Xantphos (59 mg, 0.10 mmol) and DBU (388 mul, 2.56 mmol) in toluene (2.0 ml) was subjected to microwave irradiation at 15O0C for 10 minutes. The reaction mixture was concentrated and the resultant residue absorbed onto HM-N before being purified by flash chromatography (Si-SPE, cyclohexane: ethyl acetate, gradient 100:0 to 0: 100) to afford the title compound as a white solid (231 mg, 57%). LCMS (method B): Rx = 3.22 min, M+H+ = 397/399.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2,5-difluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 112279-60-4,Some common heterocyclic compound, 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, molecular formula is C6H4BrF2N, 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.

EXAMPLE 197 5,8-Difluoro-1,2-dihydro-6-(3-nitrophenyl)-2,2,4-trimethylquinoline (Compound 297, structure 83 of Scheme XXI, where R1 =R3-5 =R7 =R9 =H, R2 =nitro, R6 =R8 =fluoro) This compound was prepared by the same procedure as described in the synthesis of Compound 291 (EXAMPLE 191) from 4-bromo-2,5-difluoroaniline (32 mg, 0.13 mmol) and 3-nitrobenzeneboronic acid (167 mg, 1.0 mmol) to afford 3 mg (10%) of Compound 297 as a colorless oil. Data for Compound 297: 1 H NMR (400 MHz, CDCl3) 8.33 (t, J=1.6, 1H), 8.14 (dd, J=8.0, 1.6, 1H), 7.78 (d, J=8.0, 1H), 7.57 (t, J=8.0, 1H), 6.94 (dd, J=10.8, 6.3, 1H), 5.37 (s, 1H), 4.16 (bs, 1H), 2.17 (dd, J=7.0, 1.3, 3H), 1.34 (s, 6H).

The synthetic route of 112279-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 112279-60-4,Some common heterocyclic compound, 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, molecular formula is C6H4BrF2N, 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.

EXAMPLE 197 5,8-Difluoro-1,2-dihydro-6-(3-nitrophenyl)-2,2,4-trimethylquinoline (Compound 297, structure 83 of Scheme XXI, where R1 =R3-5 =R7 =R9 =H, R2 =nitro, R6 =R8 =fluoro) This compound was prepared by the same procedure as described in the synthesis of Compound 291 (EXAMPLE 191) from 4-bromo-2,5-difluoroaniline (32 mg, 0.13 mmol) and 3-nitrobenzeneboronic acid (167 mg, 1.0 mmol) to afford 3 mg (10%) of Compound 297 as a colorless oil. Data for Compound 297: 1 H-NMR(400 MHz, CDCl3) 8.33 (t, J=1.6, 1H), 8.14 (dd, J=8.0, 1.6, 1H), 7.78 (d, J=8.0, 1H), 7.57 (t, J=8.0, 1H), 6.94 (dd, J=10.8, 6.3, 1H), 5.37 (s, 1H), 4.16 (bs, 1H), 2.17 (dd, J=7.0, 1.3, 3H), 1.34 (s, 6H).

The synthetic route of 112279-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, belongs to bromides-buliding-blocks 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 112279-60-4, category: bromides-buliding-blocks

A degassed solution of ethyl 3-(trifluoromethanesulfonyloxy)furo [3,2- c]pyridine-2-carboxylate (678 mg, 2.00 mmol), 4-bromo-2,5-difluoroaniline (670 mg, 3.22 mmol), Pd2dba3 (147 mg, 0.160 mmol), Xantphos (97.0 mg, 0.168 mmol) and finely powdered K3PO4 (793 mg, 3.74 mmol) in toluene (7.5 ml) was heated in a sealed tube at 1050C overnight. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate (15 ml) and filtered through a plug of silica gel (15 ml packed in ethyl ether). After washing the filter cake with more ethyl acetate (20 ml), the filtrate was dried over magnesium sulfate and concentrated in vacuo to give a brown oil. The residue was purified by flash chromatography (silica gel, using using 5:3:2 hexane-methylene chloride-ethyl ether) to afford the title compound as a tan solid (329 mg, 41%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 112279-60-4,Some common heterocyclic compound, 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, molecular formula is C6H4BrF2N, 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.

A mixture OF 4-(6-CHLORO-5-METHYL-PYRIMIDIN-4-YLOXY)-PIPERIDINE-1-CARBOXYLIC acid isopropyl ester (1.03 g, 3.28 mmol), palladium acetate (74 mg, 0.33 mmol), biphenyl-3-yl-di-tert-butyl- phosphane (9.7 mg, 0.033 mmol), sodium tert-butoxide (708 mg, 7.36 mmol), and 4-bromo-2,5- difluoro-phenylamine (706 mg, 3. 39 mmol) in 15 mL dioxane was heated in microwave for 1 hour at 120C. Solids were filtered off and mixture was purified by column chromatography (hexane/AcOEt) and crystallized from HEXANE/ACOET TO give compound A86 as a tanned solid (652 mg, 41%). 1H NMR (CDC13, 400 MHz) 5 1.04-1. 05 (d, 6H), 1.50-1. 61 (M, 2H), 1.74-1. 82 (M, 2H), 1.89 (s, 3H), 3.16-3. 22 (M, 2H), 3.51-3. 60 (M, 2H), 4.69-4. 76 (M, 1H), 5.09-5. 15 (M, 1H), 6.34-6. 36 (M, 1H), 7.07- 7.11 (M, 1H), 8.15 (s, 1H), 8. 34-8. 38 (M, 1H). Exact mass calculated for C2OH23BRF2N403 484.09, found 485.2 (MH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,5-difluoroaniline, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary