2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid

Base Information

• Chemical Name: 2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid
• CAS No.: 143879-83-8
• Molecular Formula: C₉H₁₀Cl₂FNO₂Si
• Molecular Weight: 282.174
• Mol file: 143879-83-8.mol

Synonyms:2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid

Chemical Property of 2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid

There total 1 articles about 2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid 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:

chloro-trimethyl-silane (75-77-4) + 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (82671-06-5) → 2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid (143879-83-8)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, hexane, -73 deg C, 3 h, 2.) THF, hexane, from -66 deg C, 1 h;

DOI:10.1002/jhet.5570290453

Reference yield:

2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid (143879-83-8) → 7-(N-tert-butyloxycarbonylpiperazin-1-yl)-6-fluoro-5-formyl-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 7 steps

1: 19.7 g / oxalyl dichloride, DMF / CH₂Cl₂ / 5 h / 25 °C

2: 1.) BuLi / 1.) THF, hexane, -25 deg C, 30 min, 2.) THF, hexane, -70 deg C, 1.5 h

3: 30.6 g / acetic anhydride / 120 °C

4: ethanol / 2 h / Ambient temperature

5: 55 percent / NaH / dioxane / 1.5 h / 45 °C

6: 24 percent / POCl₃ / 1,2-dichloro-benzene / 2 h / 90 - 100 °C

7: 58 percent / acetonitrile / 2 h / 40 °C

With n-butyllithium; oxalyl dichloride; acetic anhydride; sodium hydride; N,N-dimethyl-formamide; trichlorophosphate; In 1,4-dioxane; ethanol; dichloromethane; 1,2-dichloro-benzene; acetonitrile;

DOI:10.1002/jhet.5570290453

Reference yield:

2,6-dichloro-4-trimethylsilyl-5-fluoronicotynic acid (143879-83-8) → 7-(N-tert-butyloxycarbonylpiperazin-1-yl)-6-fluoro-5-hydroxymethyl-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester

Guidance literature:

Multi-step reaction with 8 steps

1: 19.7 g / oxalyl dichloride, DMF / CH₂Cl₂ / 5 h / 25 °C

2: 1.) BuLi / 1.) THF, hexane, -25 deg C, 30 min, 2.) THF, hexane, -70 deg C, 1.5 h

3: 30.6 g / acetic anhydride / 120 °C

4: ethanol / 2 h / Ambient temperature

5: 55 percent / NaH / dioxane / 1.5 h / 45 °C

6: 24 percent / POCl₃ / 1,2-dichloro-benzene / 2 h / 90 - 100 °C

7: 58 percent / acetonitrile / 2 h / 40 °C

8: 30 percent / NaBH₄ / methanol / 1.5 h / 0 °C

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; acetic anhydride; sodium hydride; N,N-dimethyl-formamide; trichlorophosphate; In 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-benzene; acetonitrile;

DOI:10.1002/jhet.5570290453

upstream raw materials:

chloro-trimethyl-silane

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid

Refernces