tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
• CAS No.: 1350324-11-6
• Molecular Formula: C₂₁H₁₉BrClF₃N₂O₃
• Molecular Weight: 519.746
• Mol file: 1350324-11-6.mol

Synonyms:tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Chemical Property of tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

There total 11 articles about tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate 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:

ethyl 2-chloro-2,2-difluoroacetate (383-62-0) + tert-butyl 5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-hydroxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1350324-13-8) → tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1350324-11-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 6h; sealed tube;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1350324-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -40 - -10 °C

1.2: 17 h / -40 - 20 °C

2.1: piperidine / dichloromethane / 16 h / 20 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 °C / sealed tube

With piperidine; sodium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine (1350322-47-2) → tert-butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]-ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1350324-11-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: boron tribromide / dichloromethane / 18.16 h / -78 - 20 °C

1.2: 0.5 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -40 - -10 °C

2.2: 17 h / -40 - 20 °C

3.1: piperidine / dichloromethane / 16 h / 20 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 °C / sealed tube

With piperidine; boron tribromide; sodium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

di-tert-butyl dicarbonate

ethyl 2-chloro-2,2-difluoroacetate

tert-butyl 5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-hydroxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

Downstream raw materials:

(2R)-3-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-3,5-dimethyl-1H-pyrazol-1-yl]propane-1,2-diol

(2S)-3-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]propane-1,2-diol

trans-4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]cyclohexanol

trans-4-[4-(3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methyl-1H-pyrazol-1-yl]cyclohexanecarboxamide