Benzoic acid, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-6-yl)-, Methyl ester

Base Information

• Chemical Name: Benzoic acid, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-6-yl)-, Methyl ester
• CAS No.: 1011717-00-2
• Molecular Formula: C14H10ClN3O2
• Molecular Weight: 287.705
• Hs Code.: 2933990090
• Mol file: 1011717-00-2.mol

Synonyms:Benzoic acid, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-6-yl)-, Methyl ester

Chemical Property of Benzoic acid, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-6-yl)-, Methyl ester

Chemical Property:

• PKA: 10.34±0.50(Predicted)
• PSA: 67.87000
• Density: 1.414±0.06 g/cm3(Predicted)
• LogP: 3.06490

Purity/Quality:

≥99% ^*data from raw suppliers

Methyl4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-6-yl)-, Methyl ester

There total 5 articles about Benzoic acid, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-6-yl)-, Methyl ester 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: 93.0%

methyl 4-(4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate (1011716-97-4) → methyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate (1011717-00-2)

Guidance literature:

With trichlorophosphate; at 110 ℃; for 3h;

Reference yield: 48.0%

6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine + methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (171364-80-0) → methyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate (1011717-00-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; In 1,4-dioxane; water; at 90 ℃; for 16h; Inert atmosphere;

Reference yield:

methyl 4-(2-bromoacetyl)benzoate (56893-25-5) → methyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate (1011717-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium / 0.5 h

1.2: 0.5 h / 20 °C

1.3: 20 °C

2.1: formic acid / N,N-dimethyl-formamide / 150 °C

3.1: trichlorophosphate / Reflux

With formic acid; sodium; trichlorophosphate; In N,N-dimethyl-formamide;

upstream raw materials:

methyl 4-(4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate

ethyl 2-amino-5-(4-(methoxycarbonyl)phenyl)-1H-pyrrole-3-carboxylate

methyl 4-(2-bromoacetyl)benzoate

methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Downstream raw materials:

methyl 4-(4-((R)-1-phenylethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoate

4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzoic acid

[4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl]-(4-methylpiperazin-1-yl)methanone

Refernces

• 1、 -. "Substituted Hetero-Bicyclic Compounds, Compositions and Medicinal Applications Thereof". Paragraph 0232. . Retrieved 2015/03/16.
• 2、 -. "SUBSTITUTED HETERO-BICYCLIC COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF". Page/Page column 70-71. . Retrieved 2013/11/05.