tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate

Base Information

• Chemical Name: tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate
• CAS No.: 1260494-72-1
• Molecular Formula: C₃₀H₃₂ClN₃O₄
• Molecular Weight: 534.055
• Mol file: 1260494-72-1.mol

Synonyms:tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate

Chemical Property of tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate

There total 10 articles about tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-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: 49.0%

tert-butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (1260494-02-7) + 4-{[(4-chlorophenyl)methyl]oxy}-2(1H)-pyridinone (191090-84-3) → tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate (1260494-72-1)

Guidance literature:

With 8-quinolinol; caesium carbonate; copper(l) iodide; In dimethyl sulfoxide; at 135 ℃; Inert atmosphere;

Reference yield:

3-bromophenylhydrazine hydrochloride (27246-81-7) → tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate (1260494-72-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrogenchloride / ethanol; water / 1 h / Reflux

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; tetrahydrofuran / 0.75 h / 0 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C / Inert atmosphere

3.2: 2 h / 20 °C

4.1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 20 h / Reflux

5.1: diphenyl phosphoryl azide / 4.5 h / 100 °C

5.2: Sonication

5.3: pH 7

6.1: borane-THF / tetrahydrofuran / 21 h / Reflux

6.2: 4.5 h / Reflux

7.1: caesium carbonate; 8-quinolinol / copper(l) iodide / dimethyl sulfoxide / 135 °C / Inert atmosphere

With hydrogenchloride; 8-quinolinol; borane-THF; diphenyl phosphoryl azide; hydroxylamine hydrochloride; sodium acetate; sodium hydride; caesium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) iodide; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;

Reference yield:

para-Chlorobenzyl alcohol (873-76-7) → tert-butyl 8-(4-(4-chlorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4, 3-b]indole-2 (1H)-carboxylate (1260494-72-1)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate; 1,10-Phenanthroline / copper(l) iodide / toluene / 105 °C

2: formic acid; ammonium acetate / water / 96 h / Reflux

3: caesium carbonate; 8-quinolinol / copper(l) iodide / dimethyl sulfoxide / 135 °C / Inert atmosphere

With 8-quinolinol; formic acid; 1,10-Phenanthroline; ammonium acetate; caesium carbonate; copper(l) iodide; In water; dimethyl sulfoxide; toluene;

upstream raw materials:

3-bromophenylhydrazine hydrochloride

para-Chlorobenzyl alcohol

cyclohexanone

2-chloro-4-iodopyridine

Downstream raw materials:

4-(4-Chlorobenzyloxy)-1-(6-methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one hydrochloride

Refernces