7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine

Base Information

• Chemical Name: 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine
• CAS No.: 721965-55-5
• Molecular Formula: C₃₅H₃₃NO₆
• Molecular Weight: 563.65
• Mol file: 721965-55-5.mol

Synonyms:7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine

Chemical Property of 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine

There total 1 articles about 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[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: 89.0%

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine (496047-46-2) → 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine (721965-55-5)

Guidance literature:

6-bromo-2,3-dihydro-1-benzofuran; With magnesium; In tetrahydrofuran;

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/j.bmc.2004.02.033

Reference yield:

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine (721965-55-5) → 5-(2,3-dihydro-benzofuran-6-yl)-7-(2-hydroxy-4-methoxy-phenyl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 4-(dimethylamino)pyridine / CHCl₃ / 1 h / 20 °C

2: 189 g / H₂; NaHCO₃ / Pd(OH)2/C / tetrahydrofuran; ethanol / 45 h / 20 °C / 760 Torr

3: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C

With dmap; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; palladium dihydroxide; In tetrahydrofuran; ethanol; chloroform; tert-butyl alcohol;

DOI:10.1016/j.bmc.2004.02.033

Reference yield:

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine (721965-55-5) → 5-(2,3-dihydro-benzofuran-6-yl)-7-[2-(1,2-dihydroxy-ethyl)-4-methoxy-phenyl]-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: 4-(dimethylamino)pyridine / CHCl₃ / 1 h / 20 °C

2.1: 189 g / H₂; NaHCO₃ / Pd(OH)2/C / tetrahydrofuran; ethanol / 45 h / 20 °C / 760 Torr

3.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C

4.1: 172 g / 4-(dimethylamino)pyridine / CHCl₃ / 0.5 h / 0 °C

5.1: dichloro[bis(triphenylphosphine)]palladium; LiCl / dimethylformamide / 4 h / 125 °C

5.2: 112 g / KF / dimethylformamide; H₂O; ethyl acetate / 0.5 h / 20 °C

6.1: OsO₄; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O / 12 h / 20 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; osmium(VIII) oxide; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; lithium chloride; palladium dihydroxide; In tetrahydrofuran; ethanol; chloroform; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5.1: Stille coupling;

DOI:10.1016/j.bmc.2004.02.033

upstream raw materials:

6-bromo-2,3-dihydro-1-benzofuran

7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine