1H-PYRROLO[2,3-B]PYRIDIN-5-OL

Base Information

• Chemical Name: 1H-PYRROLO[2,3-B]PYRIDIN-5-OL
• CAS No.: 98549-88-3
• Molecular Formula: C7H6N2O
• Molecular Weight: 134.137
• Hs Code.: 2933990090
• Mol file: 98549-88-3.mol

Synonyms:1H-PYRROLO[2,3-B]PYRIDIN-5-OL;

Chemical Property of 1H-PYRROLO[2,3-B]PYRIDIN-5-OL

Chemical Property:

• Melting Point: 219-220oC
• Boiling Point: 381.8±42.0 °C(Predicted)
• PKA: 6.93±0.20(Predicted)
• PSA: 48.91000
• Density: 1.434g/cm3
• LogP: 1.26850
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98% ^*data from raw suppliers

1H-?Pyrrolo[2,?3-?b]?pyridin-?5-?ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1H-?Pyrrolo[2,?3-?b]?pyridin-?5-?ol is a reagent used in the synthesis of potent VEGFR-2 inhibitors. 7-Azaindole derivative identified as an intermediate in the synthesis of Venetoclax (A112430), a potent and selective BCL-2 inhibitor that achieves potent antitumour activity while sparing platelets.

Technology Process of 1H-PYRROLO[2,3-B]PYRIDIN-5-OL

There total 1 articles about 1H-PYRROLO[2,3-B]PYRIDIN-5-OL 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:

4-chloro-7-azaindole (55052-28-3) → 5-hydroxypyrrolo[2,3-b]pyridine (98549-88-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: 93.5 percent / tetrahydrofuran; hexane / 18 h / 80 °C

2.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

2.2: 65 percent / (R)-camphorsulfonyl oxaziridine / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C

3.1: 49 percent / zinc; acetic acid / ethyl acetate / 18 h / 20 °C

4.1: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hydride; acetic acid; zinc; In tetrahydrofuran; hexane; cyclohexane; ethyl acetate;

DOI:10.1016/j.tetlet.2004.01.122

Reference yield: 92.4%

5-hydroxypyrrolo[2,3-b]pyridine (98549-88-3) + 4-bromo-2-fluoro-benzoic acid tert-butyl ester (889858-12-2) → 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoic acid tert-butyl ester (1628047-84-6)

Guidance literature:

With potassium carbonate; In acetonitrile; at 80 ℃; for 0.5h; Temperature;

Reference yield: 92.0%

5-hydroxypyrrolo[2,3-b]pyridine (98549-88-3) + 4-bromo-2-fluoro-N,N-bis[(4-methoxyphenyl)methyl]benzenesulfonamide (903578-46-1) → 4-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzenesulfonamide

Guidance literature:

With sodium t-butanolate; In N,N-dimethyl-formamide; at 20 ℃;

upstream raw materials:

4-chloro-7-azaindole

Downstream raw materials:

5-phenoxy-1H-pyrrolo[2,3-b]pyridine

tert-butyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((4′-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoate

2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoic acid tert-butyl ester

2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4-((4’-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methyl)piperazin-1-yl)benzoic acid methyl ester

Refernces