3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 892414-47-0
• Molecular Formula: C₈H₅F₃N₂
• Molecular Weight: 186.136
• DSSTox Substance ID: DTXSID60468980
• Nikkaji Number: J2.422.540B
• Wikidata: Q72512860
• Mol file: 892414-47-0.mol

Synonyms:892414-47-0;3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine;3-Trifluoromethyl-1H-pyrrolo[2,3-b]pyridine;3-TRIFLUOROMETHYL-7-AZAINDOLE;3-TRIFLUOROMETHYLPYRROLO[2,3-B]PYRIDINE;MFCD12024500;SCHEMBL423854;3-(Trifluoromethyl)-7-azaindole;DTXSID60468980;CS-M2167;AKOS015919239;PB26756;AS-38567;SY098660;FT-0655702;A843100

Chemical Property of 3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• PKA: 12.04±0.40(Predicted)
• PSA: 28.68000
• Density: 1.447±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 2.58170
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 186.04048265
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

97% ^*data from raw suppliers

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(NC=C2C(F)(F)F)N=C1

Technology Process of 3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

There total 6 articles about 3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-(trifluoromethyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-3-ol (892414-46-9) → 3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (892414-47-0)

Guidance literature:

3-(trifluoromethyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-3-ol; With pyridine; thionyl chloride; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

With sodium carbonate; In tetrahydrofuran; water; pH=6; Cooling with ice water;

Reference yield: 63.0%

7-Azaindole (271-63-6) + 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate (1961266-44-3) → 3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (892414-47-0) + 2-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (918514-78-0)

Guidance literature:

With [(Tp)Ni^IV(CF₃)₃]; In dimethyl sulfoxide; at 25 ℃; for 24h; Overall yield = 70 percent; Overall yield = 79 percentSpectr.; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1021/jacs.9b06383

Reference yield:

1,1,1-trifluoro-2-(2-fluoropyridin-3-yl)-3-nitropropan-2-ol (892414-45-8) → 3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (892414-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / H₂ / Raney-nickel / ethanol / 20 °C

2: 83 percent / thionyl chloride; pyridine / CH₂Cl₂ / 20 °C

With pyridine; thionyl chloride; hydrogen; nickel; In ethanol; dichloromethane;

DOI:10.1055/s-2006-958935

upstream raw materials:

3-(trifluoromethyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-3-ol

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol

1,1,1-trifluoro-2-(2-fluoropyridin-3-yl)-3-nitropropan-2-ol

2-fluoropyridine

Downstream raw materials:

5-bromo-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

C₁₅H₈BrF₃N₂O

benzyl (6-chloro-3-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)(2-fluoro-4-nitrophenyl)acetate