BENZYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE

Base Information

• Chemical Name: BENZYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• CAS No.: 1020173-39-0
• Molecular Formula: C17H18BNO4
• Molecular Weight: 311.145
• Mol file: 1020173-39-0.mol

Synonyms:BENZYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE;2-((BENZYLOXY)CARBONYL)-1,2,3,4-TETRAHYDROISOQUINOLIN-6-YL-6-BORONIC ACID;(2-((Benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)boronic acid

Chemical Property of BENZYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE

Chemical Property:

• PSA: 70.00000
• LogP: 0.99920

Purity/Quality:

95%-98% ^*data from raw suppliers

(2-((Benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)boronic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BENZYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE

There total 2 articles about BENZYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-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: 82.0%

benzyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1020174-05-3) → (2-((benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)boronic acid (1020173-39-0)

Guidance literature:

benzyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate; With sodium periodate; In tetrahydrofuran; water; at 25 ℃; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; water; for 2.5h;

Reference yield:

benzyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate → (2-((benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)boronic acid (1020173-39-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere

2: sodium periodate; ammonium acetate / water; acetone / 19 h / 20 °C

With sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium acetate; potassium acetate; In 1,4-dioxane; water; acetone; 1: |Suzuki Coupling;

Reference yield: 68.2%

(2-((benzyloxy)carbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)boronic acid (1020173-39-0) + (S)-isopropyl 2-(5-bromo-4-(4,4-difluorochroman-6-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate → (S)-benzyl 6-(5-(1-(tert-butoxy)-2-isopropoxy-2-oxoethyl)-4-(4,4-difluorochroman-6-yl)-2,6-dimethylpyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; at 85 ℃; for 18h;

upstream raw materials:

benzyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Downstream raw materials:

benzyl 6-(3-tert-butyl-5-(ethoxycarbonyl)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

1-(2-(benzyloxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-3-tert-butyl-1H-pyrazole-5-carboxylic acid

benzyl 6-(3-tert-butyl-5-((2,2,2-trichloroethoxy)carbonyl)amino-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

benzyl 6-(3-tert-butyl-5-(3-(2-fluoro-4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenyl)ureido)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate