methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate

Base Information

• Chemical Name: methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate
• CAS No.: 782499-32-5
• Molecular Formula: C₂₅H₃₁NO₃
• Molecular Weight: 393.526
• Mol file: 782499-32-5.mol

Synonyms:methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate

Chemical Property of methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate

There total 7 articles about methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-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:

methyl 5-amino-2-methylbenzoate (18595-12-5) → methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate (782499-32-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 34 percent / iodomonochloride; calcium carbonate / CH₂Cl₂; methanol; H₂O / 20 °C

2.1: diethylamine; dichlorobis(triphenylphosphino)palladium; copper iodide / dimethylformamide / 2 h / 20 °C

3.1: 3.4 mg / dichlorobis(benzonitrile)palladium / dimethylformamide / 0.5 h / 80 °C

4.1: phosphorous oxychloride / 0.5 h / 5 °C

4.2: 99 percent / 0.83 h / 5 °C

5.1: 44 percent / cesium carbonate / dimethylformamide / 19.5 h / 20 °C

6.1: sodium borohydride / methanol / 0.17 h / 5 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; Iodine monochloride; caesium carbonate; diethylamine; calcium carbonate; trichlorophosphate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja035540l

Reference yield:

methyl [3-formyl-2-pentyl-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate (618881-41-7) → methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate (782499-32-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 5 ℃; for 0.166667h;

DOI:10.1021/ja035540l

Reference yield:

methyl 2-methyl-5-nitrobenzoate (77324-87-9) → methyl [3-hydroxymethyl-2-(1-pentyl)-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate (782499-32-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / Pd/C; H₂ / methanol / 2 h / 20 °C

2.1: 34 percent / iodomonochloride; calcium carbonate / CH₂Cl₂; methanol; H₂O / 20 °C

3.1: diethylamine; dichlorobis(triphenylphosphino)palladium; copper iodide / dimethylformamide / 2 h / 20 °C

4.1: 3.4 mg / dichlorobis(benzonitrile)palladium / dimethylformamide / 0.5 h / 80 °C

5.1: phosphorous oxychloride / 0.5 h / 5 °C

5.2: 99 percent / 0.83 h / 5 °C

6.1: 44 percent / cesium carbonate / dimethylformamide / 19.5 h / 20 °C

7.1: sodium borohydride / methanol / 0.17 h / 5 °C

With bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; palladium on activated charcoal; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; hydrogen; Iodine monochloride; caesium carbonate; diethylamine; calcium carbonate; trichlorophosphate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja035540l

upstream raw materials:

methyl [3-formyl-2-pentyl-1-(2-phenylethyl)-5-methyl]indole-6-carboxylate

methyl 2-methyl-5-nitrobenzoate

methyl 5-amino-2-methylbenzoate

methyl (3-amino-4-iodo-6-methyl)benzoate