Pyridine, 2-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-6-methoxy-

Base Information

• Chemical Name: Pyridine, 2-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-6-methoxy-
• CAS No.: 183433-64-9
• Molecular Formula: C11H14ClNO3
• Molecular Weight: 243.69
• Mol file: 183433-64-9.mol

Synonyms:

Chemical Property of Pyridine, 2-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-6-methoxy-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pyridine, 2-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-6-methoxy-

There total 2 articles about Pyridine, 2-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-6-methoxy- 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: 20.0%

6-Chloro-4-(2-ethyl-[1,3]dioxolan-2-yl)-2-methoxy-pyridine-3-carbaldehyde (183433-65-0) → 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxypyridine (183433-64-9) + [6-Chloro-4-(2-ethyl-[1,3]dioxolan-2-yl)-2-methoxy-pyridin-3-yl]-methanol (183433-66-1)

Guidance literature:

With sodium tetrahydroborate; tetrabutyl-ammonium chloride; In water; for 18h;

DOI:10.1021/jo970173f

Reference yield:

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxypyridine (183433-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / tetrahydrofuran / 1 h / 0 °C

2: 100 percent / TMSCl / 12 h / Ambient temperature

3: 89 percent / methanol / 20 h / Heating

With chloro-trimethyl-silane; In tetrahydrofuran; methanol;

DOI:10.1021/jo970173f

Reference yield:

6-chloro-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxypyridine (183433-64-9) → irinotecan (97682-44-5,130144-33-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h

2: 71 percent / NaBH₄, n-Bu₄NCl / H₂O / 18 h

3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C

4: 89 percent / Pd(OAc)2, K₂CO₃, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr

6: 92 percent / OsO₄, Me₃NO*2H₂O / 2-methyl-propan-2-ol / 24 h / 40 °C

7: 76 percent / PS-30 catalyst / various solvent(s) / 48 h

8: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO₃ / CH₂Cl₂; H₂O / 0.67 h

9: 96 percent / H₂ / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature

10: 99 percent / TEMPO, KBr, NaHCO₃, NaOCl / CH₂Cl₂; H₂O / 0.5 h

11: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C

12: 74 percent / Cs₂CO₃ / dimethylsulfoxide / 21 h / 47 - 50 °C

13: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C

14: p-TSA*H₂O / toluene; acetic acid / 18 h / 95 - 100 °C

15: pyridine / 2 h / 20 - 25 °C

With palladium diacetate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; 4-acetoxy-2,2,6,6-tetramethylpiperidine-1-oxyl; trimethylamine-N-oxide; PS-30 catalyst; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; sodium iodide; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; trifluoroacetic acid; tert-butyl alcohol;

DOI:10.1021/jo970173f

upstream raw materials:

6-Chloro-4-(2-ethyl-[1,3]dioxolan-2-yl)-2-methoxy-pyridine-3-carbaldehyde

2,6-dichloropyridine-4-carboxylic acid

Downstream raw materials:

6-Chloro-4-(2-ethyl-[1,3]dioxolan-2-yl)-2-methoxy-pyridine-3-carbaldehyde

8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one

6-chloro-2-methoxy-3-methyl-4-[1-(phenylmethoxy)propyl]pyridine

2,3-dihydro-6-methyl-7-[1-(phenylmethoxy)-propyl]-1,5-indolizinedione

Refernces

• 1、 Henegar,Ashford,Baughman,Sih,Gu. "Practical asymmetric synthesis of (S)-4,ethyl-7,8-dihydro-4-hydroxy-1H- pyrano[3,4-f]indolizine-3,6,10(4H)-trione, a key intermediate for the synthesis of Irinotecan and other camptothecin analogs". . p. 6588 - 6597. Retrieved 2007/10/03.