HCID 701019, Verbindung → HCID 86664325, Verbindung

HRID 1753887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753887
Cl[C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH3:19])[CH:5]=[C:4]([Cl:20])[N:3]=1.[CH:21]([Mg]Cl)([CH3:23])[CH3:22]>C1COCC1>[Cl:20][C:4]1[N:3]=[C:2]([CH:21]([CH3:23])[CH3:22])[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH3:19])[CH:5]=1

Komponenten

4

Edukt 2

HCID 701019HCID 701019, VerbindungHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 86664325HCID 86664325, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of 6.0 g (18.3 mmol) 2,6-dichloro-N-(4-chlorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide (synthesized according to the method described in section a) of example 2) in THF (180 ml) and NMP (60 ml) was degassed for 30 min followed by the addition of 1.3 g (3.7 mmol) Fe(acac)3. This mixture was degassed again for 20 min. At −40° C. 137 ml (2M in THF, 274 mmol) isopropylmagnesiumchloride was added dropwise over 1 h. The reaction mixture was allowed to reach 0° C. and was quenched at this temperature with a sat. aq. NH4Cl sol. followed by stirring at 10° C. for 30 min. Then the mixture was diluted with EtOAc and the organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 2.45 g (7.3 mmol, 40%) 6-chloro-N-(4-chlorobenzyl)-2-isopropyl-4-methyl-pyridine-3-carboxylic amide.

Aufarbeitung

  1. customNMP (60 ml) was degassed for 30 min
  2. customThis mixture was degassed again for 20 min
  3. customAt −40° C
  4. customto reach 0° C.
  5. customwas quenched at this temperature with a sat. aq. NH4Cl sol.
  6. additionThen the mixture was diluted with EtOAc
  7. customthe organic layer was separated
  8. washwashed with water and brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by CC (hexane/EtOAc 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-6fbb11c54a894de581509e9442ae45d8
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09168259B2

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