4-chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine

Base Information

• Chemical Name: 4-chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine
• CAS No.: 178268-92-3
• Molecular Formula: C8H7ClN2
• Molecular Weight: 166.60800
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70444634
• Wikidata: Q82262824
• Mol file: 178268-92-3.mol

Synonyms:4-chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine;178268-92-3;4-CHLORO-6-METHYL-5-AZAINDOLE;1H-Pyrrolo[3,2-c]pyridine, 4-chloro-6-methyl-;MFCD12401559;AMY9631;DTXSID70444634;AKOS024260873;AS-40433;SY241509;CS-0096466;1h-pyrrolo[3,2-c]pyridine,4-chloro-6-methyl-

Chemical Property of 4-chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine

Chemical Property:

• PSA: 28.68000
• LogP: 2.52470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 166.0297759
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

97% purity ^*data from raw suppliers

4-Chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=CN2)C(=N1)Cl

Technology Process of 4-chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine

There total 2 articles about 4-chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine 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: 83.0%

6-Methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (178268-91-2) → 4-Chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine (178268-92-3)

Guidance literature:

With trichlorophosphate; at 180 - 185 ℃; for 6h;

DOI:10.1002/jhet.5570330215

Reference yield:

1-Benzyl-6-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (178268-90-1) → 4-Chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine (178268-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Na, liquid NH₃ / 1.5 h / -78 °C

2: 83 percent / phosphorus oxychloride / 6 h / 180 - 185 °C

With ammonia; sodium; trichlorophosphate;

DOI:10.1002/jhet.5570330215

Reference yield:

4-Chloro-6-methyl-1H-pyrrolo[3,2-c]pyridine (178268-92-3) → C24H32FN3O2 (949536-20-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / dimethylformamide

2.1: POCl₃ / Heating

3.1: BuLi / tetrahydrofuran / 0.17 h / 0 °C

3.2: tetrahydrofuran / 20 °C

4.1: aq. HCl / 1.5 h / 70 °C

5.1: NaBH₄ / methanol / 1 h / 0 °C

6.1: imidazole; DMAP / dimethylformamide / 20 °C

7.1: 2-(dicyclohexylphosphino)-2'-methylbiphenyl; K₃PO₄ / Pd₂(dba)3 / 1,2-dimethoxy-ethane / 0.33 h / 100 °C / 3102.97 Torr / microwave irradiation

8.1: Et₃N*3HF / dimethylformamide / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; potassium phosphate; n-butyllithium; sodium hydride; triethylamine tris(hydrogen fluoride); 2-(dicyclohexylphosphino)-2'-methylbiphenyl; trichlorophosphate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 7.1: Buchwald amination;

DOI:10.1016/j.bmcl.2007.06.077

upstream raw materials:

6-Methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one

1-Benzyl-6-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one

Downstream raw materials:

Dibenzyl-(6-methyl-1H-pyrrolo[3,2-c]pyridin-4-yl)-amine

C₃₁H₄₃F₆N₃OSi

C₂₅H₂₉F₆N₃O

Refernces