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

Base Information

• Chemical Name: tert-butyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoate
• CAS No.: 1628047-84-6
• Molecular Formula: C₁₈H₁₇BrN₂O₃
• Molecular Weight: 389.249
• Mol file: 1628047-84-6.mol

Synonyms:tert-butyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoate;tert-butyl 4-bromo-2-{1H-pyrrolo[2,3-b]pyridin-5-yloxy}benzoate;ABT199 intermediate 2;4-Bromo-2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)benzoic acid 1,1-dimethylethyl ester

Chemical Property of tert-butyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoate

Chemical Property:

• PKA: 13.26±0.40(Predicted)
• PSA: 64.21000
• Density: 1.445±0.06 g/cm3(Predicted)
• LogP: 5.07300
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

tert-?Butyl4-?Bromo-?2-?(1H-?pyrrolo[2,?3-?b]?pyridin-?5-?yloxy)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: tert-?Butyl 4-?Bromo-?2-?(1H-?pyrrolo[2,?3-?b]?pyridin-?5-?yloxy)benzoate is used in the synthesis of apoptosis-inducing agents. Intermediate of Venetoclax (A112430), a potent and selective BCL-2 inhibitor that achieves potent antitumour activity while sparing platelets.

Technology Process of tert-butyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoate

There total 3 articles about tert-butyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoate 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: 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:

1-bromo-3-fluoro-4-iodobenzene (105931-73-5) → 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoic acid tert-butyl ester (1628047-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -5 - 0 °C

1.2: 1 h

2.1: sodium t-butanolate / N,N-dimethyl-formamide / 0 - 50 °C

With isopropylmagnesium chloride; sodium t-butanolate; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-bromobenzoic acid tert-butyl ester (1628047-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -5 - 0 °C

1.2: 1 h

2.1: sodium t-butanolate / N,N-dimethyl-formamide / 0 - 50 °C

With isopropylmagnesium chloride; sodium t-butanolate; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

5-hydroxypyrrolo[2,3-b]pyridine

4-bromo-2-fluoro-benzoic acid tert-butyl ester

1-bromo-3-fluoro-4-iodobenzene

di-tert-butyl dicarbonate

Downstream raw materials:

[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]

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)-N-((3-nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)phenyl)sulfonyl)benzamide

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