5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde

Base Information

• Chemical Name: 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde
• CAS No.: 1260667-91-1
• Molecular Formula: C7H8N2O
• Molecular Weight: 136.15122
• Mol file: 1260667-91-1.mol

Synonyms:5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde

Chemical Property of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde

Chemical Property:

• PSA: 34.89000
• LogP: 0.64180

Purity/Quality:

NLT 98% ^*data from raw suppliers

5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde

There total 5 articles about 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde 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: 88.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole (174790-35-3) → 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde (1260667-91-1)

Guidance literature:

3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.5h;

DOI:10.3987/COM-17-13772

Reference yield: 45.5%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole (107862-65-7) → 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde (1260667-91-1)

Guidance literature:

With trichlorophosphate; In 1,2-dichloro-ethane; at 4 ℃; Inert atmosphere; Reflux;

DOI:10.1021/acs.jmedchem.6b01839

Reference yield:

5-(3-chloropropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole → 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carbaldehyde (1260667-91-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / ethyl acetate / 2 h / 60 °C

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 0.5 h / -78 - 0 °C

With hydrogenchloride; N-Bromosuccinimide; n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.3987/COM-17-13772

upstream raw materials:

N,N-dimethyl-formamide

5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole

3-bromo-5,6-dihydro-4H-pyrrolo<1,2-b>pyrazole

Refernces

• 1、 Denny, R. Aldrin,Flick, Andrew C.,Coe, Jotham,Langille, Jonathan,Basak, Arindrajit,Liu, Shenping,Stock, Ingrid,Sahasrabudhe, Parag,Bonin, Paul,Hay, Duncan A.,Brennan, Paul E.,Pletcher, Mathew,Jones, Lyn H.,Chekler, Eugene L. Piatnitski. "Structure-Based Design of Highly Selective Inhibitors of the CREB Binding Protein Bromodomain". . p. 5349 - 5363. Retrieved 2017/07/22.