Production Method 1

917772-69-1

917471-30-8

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Toluene ,  Tetrahydrofuran ,  Hexane ;  30 min, -40 °C; 1 h, -40 °C → -10 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  -10 °C; 1 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 7, rt

Reference

Discovery of an Orally Available, Brain Penetrant BACE1 Inhibitor That Affords Robust CNS Aβ Reduction

Stamford, Andrew W.; Scott, Jack D.; Li, Sarah W.; Babu, Suresh; Tadesse, Dawit; et al, ACS Medicinal Chemistry Letters, 2012, 3(11), 897-902

Production Method 2

13361-64-3

625-92-3

917471-30-8

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Tetrabutylammonium fluoride ,  Cuprous iodide ,  Tetrakis(triphenylphosphine)palladium Solvents: Toluene ;  rt
1.2 Reagents: Butyllithium ,  Trimethyl-1-propyn-1-ylsilane Solvents: Toluene ,  Tetrahydrofuran ;  -40 °C → -10 °C
1.3 Reagents: Ammonium hydroxide Solvents: Water

Reference

Structure based design of iminohydantoin BACE1 inhibitors: Identification of an orally available, centrally active BACE1 inhibitor

Cumming, Jared N.; Smith, Elizabeth M.; Wang, Lingyan; Misiaszek, Jeffrey; Durkin, James; et al, Bioorganic & Medicinal Chemistry Letters, 2012, 22(7), 2444-2449

Production Method 3

2250215-71-3

917471-30-8

Reaction Conditions

1.1 Solvents: Water

Reference

Process Development of a Suzuki Reaction Used in the Manufacture of Lanabecestat

Ashworth, Ian W. ; Campbell, Andrew D.; Cherryman, Janette H.; Clark, Jemma; Crampton, Alex; et al, Organic Process Research & Development, 2018, 22(12), 1801-1808

[5-(prop-1-yn-1-yl)pyridin-3-yl]boronic acid Raw materials

• 3-Bromo-5-(prop-1-yn-1-yl)pyridine
• trimethyl(prop-2-ynyl)silane
• (T-4)-[[2,2′-(Imino-κN)bis[ethanolato-κO]](2-)][5-(1-propyn-1-yl)-3-pyridinyl]boron
• 3,5-Dibromopyridine

[5-(prop-1-yn-1-yl)pyridin-3-yl]boronic acid Preparation Products

• [5-(prop-1-yn-1-yl)pyridin-3-yl]boronic acid (917471-30-8)

• 1. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 2. An insight into the origin of room-temperature ferromagnetism in SnO2 and Mn-doped SnO2 quantum dots: an experimental and DFT approach?
  Dhamodaran Manikandan,S. Amirthapandian,I. S. Zhidkov,A. I. Kukharenko,S. O. Cholakh,Ramaswamy Murugan Phys. Chem. Chem. Phys., 2018,20, 6500-6514
• 3. Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties?
  S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. Lee RSC Adv., 2014,4, 23107-23115
• 4. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
  Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378
• 5. An amphipathic trans-acting phosphorothioate RNA element delivers an uncharged phosphorodiamidate morpholino sequence in mdx mouse myotubes?
  H. V. Jain,D. Verthelyi,S. L. Beaucage RSC Adv., 2017,7, 42519-42528

• 173999-18-3((5-methylpyridin-3-yl)boronic acid)
• 1206681-16-4(5-Ethynylpyridin-3-ylboronic Acid)
• 2241867-25-2((5-(methyl-d3)pyridin-3-yl)boronic acid)
• 2377611-80-6(5-Methylpyridine-3-boronic acid hydrochloride)
• 1231934-45-4((5-(Prop-1-yn-1-yl)pyridin-3-yl)boronic acid)
• 1189372-89-1(5-(cyclopropylethynyl)pyridin-3-ylboronic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)