(S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide

Base Information

• Chemical Name: (S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide
• CAS No.: 148460-95-1
• Molecular Formula: C₂₀H₂₉BrN₂O₅
• Molecular Weight: 457.365
• Mol file: 148460-95-1.mol

Synonyms:(S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide

Chemical Property of (S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide

There total 18 articles about (S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide 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: 60.0%

(S)-N-<(1-Ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide (148460-94-0) → (S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide (148460-95-1)

Guidance literature:

With bromine; In chloroform; trifluoroacetic acid; for 4.5h; Ambient temperature;

DOI:10.1021/jo00065a015

Reference yield:

4-methoxycatechol (3934-97-2) → (S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide (148460-95-1)

Guidance literature:

Multi-step reaction with 9 steps

1: trichloroacetic acid / CH₂Cl₂ / 96 h / Ambient temperature

3: aq. NaOH / dimethylformamide / 60 °C

4: aq. NaOH / ethanol; dioxane / 1) 80 deg C, 5 h, 2) rt, overnight

5: SOCl₂, DMF / toluene / 1.5 h / 60 °C

6: CH₂Cl₂

7: 85 percent / H₂ / 5percent Pd/C / ethanol / 760 Torr

8: DMAP, pyridine / CHCl₃ / 18 h / Ambient temperature

9: Br₂, pyridine / CHCl₃ / 5 h

With pyridine; dmap; sodium hydroxide; thionyl chloride; hydrogen; bromine; N,N-dimethyl-formamide; palladium on activated charcoal; trichloroacetic acid; In 1,4-dioxane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00065a015

Reference yield:

3-Hydroxy-6-methoxysalicylic acid (148460-90-6) → (S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-6-methoxy-3-pivaloylsalicylamide (148460-95-1)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. NaOH / dimethylformamide / 60 °C

2: aq. NaOH / ethanol; dioxane / 1) 80 deg C, 5 h, 2) rt, overnight

3: SOCl₂, DMF / toluene / 1.5 h / 60 °C

4: CH₂Cl₂

5: 85 percent / H₂ / 5percent Pd/C / ethanol / 760 Torr

6: DMAP, pyridine / CHCl₃ / 18 h / Ambient temperature

7: Br₂, pyridine / CHCl₃ / 5 h

With pyridine; dmap; sodium hydroxide; thionyl chloride; hydrogen; bromine; N,N-dimethyl-formamide; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00065a015

upstream raw materials:

2-6-dimethoxybenzoic acid

4-methoxycatechol

3-Hydroxy-6-methoxysalicylic acid

1,2-Bis(1-ethoxyethoxy)-4-methoxybenzene

Downstream raw materials:

(S)-5-Bromo-N-<(1-ethyl-2-pyrrolidinyl)methyl>-3-hydroxy-6-methoxysalicylamide