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Triethylamine → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester

HRID 878060
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 878060
Br[C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[C:5]([N:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[CH3:8])=[O:6].[CH3:29]CN(CC)CC.[C:36]([O-:39])(O)=[O:37].[Na+]>CO.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:29][O:39][C:36](=[O:37])[C:2]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[C:4]([C:5]([N:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[CH3:8])=[O:6])[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 601975943-Bromo-N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamide

Produkt 1

HCID 70663193N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-isophthalamic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807
HCID 178418807, Verbindung
Katalysator
HCID 887MethanolLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-bromo-N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamide (100 mg, 213 μmol, example 74) in MeOH (1.5 mL) and EtOAc (1.5 mL) was added PdCl2(dppf)-CH2Cl2 complex (20.0 mg, 24.5 μmol, CAS RN 851232-71-8) and NEt3 (32.3 mg, 44.5 μl, 319 μmol). The reaction mixture was stirred at 100° C. at 80 bar under CO atmosphere for 18 hours. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (93 mg, 97%). MS (TurboSpray): m/z=449.088 [M+H]+.

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  3. washThe combined organic layers were washed with 30 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe compound was purified by silica gel chromatography
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Quellen und Nachweise

ORD-Eintrag
ord-82c8630fc4664c6e8e2c8043a5c431bb
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987307B2

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