3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Base Information

• Chemical Name: 3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
• CAS No.: 272107-22-9
• Molecular Formula: C14H10Br2ClN
• Molecular Weight: 387.501
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10436255
• Nikkaji Number: J1.919.542B
• Wikidata: Q72518214
• Mol file: 272107-22-9.mol

Synonyms:272107-22-9;3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene;SCHEMBL12154646;DTXSID10436255;MLUVTRZDSIHGAD-UHFFFAOYSA-N;XKA10722;8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cycloheptal[1,2-b]pyridin;AKOS016011081;CS-15845;CS-0054945;FT-0754887;D71975;6,11-Dihydro-3,10-dibromo-8-chloro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine;8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine

Chemical Property of 3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Chemical Property:

• Melting Point: 163-164 °C
• Boiling Point: 412.6±45.0 °C(Predicted)
• PKA: 2.62±0.20(Predicted)
• PSA: 12.89000
• Density: 1.750±0.06 g/cm3(Predicted)
• LogP: 4.94940
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 386.88480
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(CC3=C1C=C(C=C3Br)Cl)N=CC(=C2)Br
• Uses: 3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine is used in the synthetic preparation of lonafarnib, a potential anticancer agent.

Technology Process of 3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

There total 3 articles about 3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]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: 84.0%

3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one (193276-55-0) → 8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine (272107-22-9)

Guidance literature:

With acetic anhydride; trifluoroacetic acid; zinc; In tetrahydrofuran; at -25 - 18 ℃; for 24h;

DOI:10.1021/jo034380t

Reference yield: 82.0%

C14H11Br2ClN2 (679842-27-4) + C14H11Br2ClN2 (679842-29-6) → 8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine (272107-22-9)

Guidance literature:

With sulfuric acid; hypophosphorous acid; sodium nitrite; In methanol; water; at -5 - 65 ℃; for 12h; pH=9;

Reference yield:

3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-one hydrobromide (271252-77-8) → 8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine (272107-22-9)

Guidance literature:

3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-one hydrobromide; With sulfuric acid; nitric acid; at 35 ℃; for 2h; Inert atmosphere;

With ammonium hydroxide; In water; Further stages; Inert atmosphere;

DOI:10.1021/ol102174w

upstream raw materials:

3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one

C₁₄H₁₁Br₂ClN₂

C₁₄H₁₁Br₂ClN₂

3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-one hydrobromide

Downstream raw materials:

(R)-(+)-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11-yl)-1-piperidine

(+)-4-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11(R)-yl)-1-<(4-piperidinyl)acetyl>piperidine

(+)-1,1-dimethylethyl<<<4-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11(R)-yl)-1-piperidinyl>-carbonyl>-methyl>-1-piperidinecarboxylate

lonafarnib

Refernces

• 1、 -. "AN ENANTIOSELECTIVE PROCESS". Page 19; 22; 26. . Retrieved 2008/06/13.