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Home > Encyclopedia > 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester

2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester

2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester structure
  • CAS No:

    947249-01-6

  • Formula:

    C12H16BF3N2O2

  • Synonyms:

    2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-trifluoromethyl)pyridin-2-amine;3-(trifluoroMethyl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-aMine;6-Amino-5-(trifluoromethyl)pyridine-3-boronic acid pinacol ester;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen (6-amino-5-(trifluoromethyl)pyridin-3-yl)boronate

  • China Export:

    From 2018.11 to 2019.11, total export volume of 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester from China was 64,534,318KG while total export value was $1,953,812,763. The biggest proportion of exporting volume in the last 12 months was 11.30% in 2019.03.

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Basic Attributes

  • 947249-01-6

  • C12H16BF3N2O2

  • 306.0891296

  • 288.125702

  • 57.4

  • OQZKROYNCVLJKM-UHFFFAOYSA-N

  • 7

  • 1

  • 0.58

  • 1

Characteristics

  • 1.2±0.1 g/cm3

  • 132-134℃

  • 171.0±27.9 °C

  • 1.477

Safety Information

  • 2934999090

Production Methods

A mixture of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (180 g) and 1, 4-dioxane (3600 mL) was stirred in a flask. Bis(pinacolato)diboron (284.47 g), potassium acetate (109.95 g) and l, l-bis(diphenylphosphino)ferrocene dichloropalladium (II) DCM complex (18 g), were then added under stirring at a temperature of about 25 to 30°C. Reaction mass was heated to 95 to 100°C and maintained for 15-16 hr. After the completion of reaction, the mass was cooled to 25 to 30°C, filtered through celite bed and the bed was washed with ethyl acetate (1800 mL). The filtrate was distilled out completely under vacuum to get crude title compound (450 g). Purification The crude title compound was dissolved in methanol (1800 mL) in a round bottom flask. Charcoal (45 g) and silica gel (60-120 mesh size, 450 g) were added to the mass and maintained under stirring at a temperature of about 25 to 30°C for 1 h. The mass was filtered through celite bed and washed the bed with methanol (450 mL). The filtrate was added into a flask containing cold water (6750 mL) at 0-5°C, over a period of 1 h. The precipitated solid was filtered out, washed with cold water (900 mL). The wet compound was unloaded and dried at 45 to 50°C to obtain the title compound (209 g). Yield: 97.47percent Purity: 98.43percent An orange suspension of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (4 g, 16.60 mmol), 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi(1 , 3, 2-dioxaborolane)(5.90 g, 23.24 mmol), KOAc (4.07 g, 41 .5 mmol) and PdCIAn orange suspension of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (4 g, 16.60 mmol), 4, 4, 4′, 4′, 5, 5, 5′, 5′-octamethyl-2, 2′-bi(1, 3, 2-dioxaborolane) (5.90 g, 23.24 mmol), KOAc (4.07 g, 41.5 mmol) and PdCl[0429] To a solution of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (46B, 1.21 g, 5.0 mmol) in DME (50 mL) were added bis(pinacolato)diboron (1.65 g, 6.5 mmol), Pd(dppf)ClGeneral procedure: Commercial 1a (50mmol) was dissolved in dichloromethane (80mL), mixture was cooled to 0C, solution of NH3 in MeOH (4mol/L, 12.5mL) was added by dripping slowly, after 30min, the mixture maintained at 0C for 1h. The reaction mixture was filtered, and the insoluble material was washed with ethyl acetate (20mL) and water (30mL) to get 2a (8.66g), yield 90%. Compound 2a (50mmol) was dissolved in THF (40mL), then absolute ethyl alcohol (20mL), water (20mL), Fe (4eq) and ammonium chloride (2eq) were added. The mixture was refluxed until raw material disappeared. The reaction mixture was filtered and filter liquor was evaporated by reducing pressure to get 3a (2.4g), yield 33%. Compound 3a (17mmol) was dissolved in DMF (30mL), triethylamine (3eq) was added, and acetyl isothiocyanate (1eq) was added by dripping slowly, the mixture was stirred at room temperature for 30min, then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.5eq) was added and stirred overnight at room temperature. Pulled the mixture into ice water, using concentrated HCl regulates pH to 1, the mixture was filtered, the residue was dried and washed by water to give 4a (2.0g), yield 60%. Compound 4a (10mmol), 5a/5b/5c/5d/5e (1.2eq), 120mL 1, 4-dioxane, 10mL water, Pd(dppf)Cl2 (0.1eq), and NaHCO3 (1eq) were added to a round-bottomed flask, mixture was stirred for 12h at 90C. Solvent was removed by reduced pressure distillation, residue was purified by preparative HPLC (MeCN+0.05% TFA, H2O 0.1%+TFA), Ta-e were finally obtained from above steps, yield 0.58-5.5%.Into a vial was weighed (+-)-(1S, 2S)-N-(8-amino-6-chloro-2, 7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (60.0 mg, 0.175 mmol),

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China 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester Export Data

Data referenced from General Administration of Customs,P.R.China

2018.11-2019.11 China - America  2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester Export Data

From 2018.11 to 2019.11, total export volume of 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester from China to America was 7,780,901KG while total export value was $316,380,773. The biggest proportion of exporting volume in the last 12 months was 14.00% in 2019.01.

2018.11-2019.11 China 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester Export Data

From 2018.11 to 2019.11, total export volume of 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester from China was 64,534,318KG while total export value was $1,953,812,763. The biggest proportion of exporting volume in the last 12 months was 11.30% in 2019.03.

2018.11-2019.11 TOP10 Purchasing Countries' Export Data of Chinese 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester

From 2018.11 to 2019.11, China has exported 2-Amino-3-(trifluoromethyl)pyridine-5-boronic acid pinacol ester to 122 countries in total. Country ranks by import volume from high to low is India, America, Brazil, Korea, Japan, Indonesia, Russia, Italy, Vietnam, Germany. The highest export volume was China to India, accounting for 15.49% of the total volume of China.

Check Export Data for More Purchasing Countries

Purchasing Country Export Volume(KG) Export Percentage Export Value($)

India

18,470,088

15.49%

284,654,978

America

7,780,901

6.52%

316,380,773

Brazil

3,482,706

2.92%

56,330,619

Korea

3,279,208

2.75%

118,103,066

Japan

2,776,083

2.33%

104,179,065

Indonesia

2,652,708

2.22%

20,390,824

Russia

2,523,632

2.12%

71,402,429

Italy

1,949,908

1.64%

84,261,295

Vietnam

1,535,844

1.29%

30,876,165

Germany

1,414,521

1.19%

66,834,261

Netherlands

1,407,723

1.18%

40,043,364

Taiwan

1,336,285

1.12%

20,935,258

Belgium

1,300,937

1.09%

43,926,617

Mexico

1,203,788

1.01%

45,215,734

Pakistan

1,101,382

0.92%

39,507,765

Iran

1,044,291

0.88%

28,504,479

Turkey

905,770

0.76%

27,893,056

Singapore

780,141

0.65%

50,171,634

Thailand

719,956

0.60%

8,501,101

Australia

607,935

0.51%

14,879,125

Israel

588,856

0.49%

17,159,090

South Africa

575,310

0.48%

11,039,850

United Kingdom

501,238

0.42%

39,994,256

Malaysia

492,812

0.41%

5,439,297

Spain

446,770

0.37%

28,670,245

United Arab Emirates

304,282

0.26%

3,897,959

Canada

302,332

0.25%

21,196,696

Colombia

267,830

0.22%

8,161,669

Poland

267,574

0.22%

13,242,033

Slovenia

248,588

0.21%

18,698,953

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