Production Method 1

958230-19-8

76513-69-4

1315381-29-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0.5 h, 0 °C
1.2 0 °C; 1.5 h, 0 °C
1.3 Reagents: Water ;  0 °C

Reference

Preparation of heterotricycles as Wee 1 inhibitors for treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 2

958230-19-8

76513-69-4

1315381-29-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  10 min, 0 °C
1.2 0 °C; 0 °C → rt; 2 h, rt

Reference

Discovery of a Potent and Selective DDR1 Receptor Tyrosine Kinase Inhibitor

Kim, Hyung-Gu; Tan, Li; Weisberg, Ellen L.; Liu, Feiyang; Canning, Peter; et al, ACS Chemical Biology, 2013, 8(10), 2145-2150

Production Method 3

958230-19-8

76513-69-4

1315381-29-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  10 min, 0 °C
1.2 0 °C; 0 °C → rt; 2 h, rt

Reference

Preparation of pyrazine and pyrrolo[2,3-b]pyridine derivatives as b-raf kinase inhibitors useful in the treatment of cancer and proliferative diseases

, World Intellectual Property Organization, , ,

Production Method 4

958230-19-8

76513-69-4

1315381-29-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  10 min, cooled
1.2 30 min, rt

Reference

Preparation of tricyclic pyrrolopyridine compounds as JAK inhibitors

, World Intellectual Property Organization, , ,

Production Method 5

958230-19-8

76513-69-4

1315381-29-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ;  0 °C; 30 min, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Preparation of tricyclic heterocyclic compounds as JAK inhibitors

, World Intellectual Property Organization, , ,

1H-Pyrrolo[2,3-b]pyridine-5-carboxaldehyde, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]- Raw materials

• 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde
• 2-(Trimethylsilyl)ethoxymethyl chloride

1H-Pyrrolo[2,3-b]pyridine-5-carboxaldehyde, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]- Preparation Products

• 1H-Pyrrolo[2,3-b]pyridine-5-carboxaldehyde, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]- (1315381-29-3)

• 1. Achieving crystal-induced room temperature phosphorescence and reversible photochromic properties by strong intermolecular interactions?
  Fuming Xiao,Mengzhu Wang,Yunxiang Lei,Wenbo Dai,Yunbing Zhou,Miaochang Liu,Wenxia Gao,Xiaobo Huang,Huayue Wu J. Mater. Chem. C, 2020,8, 17410-17416
• 2. An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation??
  M. Sheykhan,S. Khani,S. Shaabanzadeh,M. Joafshan Green Chem., 2017,19, 5940-5948
• 3. An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes?
  Bo Cao,Yin Wei Chem. Commun., 2018,54, 2870-2873
• 4. 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
• 5. An interplay between electronic and structural effects on the photoluminescence decay mechanisms in LaPO4·nH2O:Tb3+ and LaPO4:Tb3+ single-crystal nanorods?
  M. T. Colomer,S. Díaz-Moreno,A. Tamayo,A. L. Ortiz J. Mater. Chem. C, 2018,6, 12643-12651

• 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)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)