tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate
• CAS No.: 934355-56-3
• Molecular Formula: C₂₃H₂₇BrFNO₄
• Molecular Weight: 480.374

Synonyms:tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate

Chemical Property of tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate

There total 5 articles about tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-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: 65.0%

1-(2-bromo-5-fluorobenzyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline (934355-46-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate (934355-56-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; dmap; In dichloromethane; at 23 ℃;

DOI:10.1002/ejoc.200600674

Reference yield:

2-(2-bromo-5-fluorophenyl)acetyl chloride (1028314-61-5) → tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate (934355-56-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 25 °C

2: POCl₃ / CH₂Cl₂ / 12 h / Heating

3: NaBH₄ / methanol / 3 h / 23 °C

4: 65 percent / iPr₂EtN / DMAP / CH₂Cl₂ / 23 °C

With sodium tetrahydroborate; triethylamine; N-ethyl-N,N-diisopropylamine; trichlorophosphate; dmap; In methanol; dichloromethane; 2: Bischler-Napieralski cyclization;

DOI:10.1002/ejoc.200600674

Reference yield:

2-(2-bromo-5-fluorophenyl) acetic acid (739336-26-6) → tert-butyl 1-(2-bromo-5-fluorobenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline-2(1H)-carboxylate (934355-56-3)

Guidance literature:

Multi-step reaction with 5 steps

1: (COCl₂); dimethylformamide / CH₂Cl₂ / 25 °C

2: Et₃N / CH₂Cl₂ / 25 °C

3: POCl₃ / CH₂Cl₂ / 12 h / Heating

4: NaBH₄ / methanol / 3 h / 23 °C

5: 65 percent / iPr₂EtN / DMAP / CH₂Cl₂ / 23 °C

With phosgene; sodium tetrahydroborate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trichlorophosphate; dmap; In methanol; dichloromethane; 3: Bischler-Napieralski cyclization;

DOI:10.1002/ejoc.200600674

upstream raw materials:

1-(2-bromo-5-fluorobenzyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline

di-tert-butyl dicarbonate

2-(2-bromo-5-fluorophenyl)acetyl chloride

2-(2-bromo-5-fluorophenyl) acetic acid

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