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Cesium carbonate → 3-(6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide

HRID 522922
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 522922
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH2:9]2)[N:3]=1.N[C:21]1[CH:30]=[CH:29][C:24]([C:25]([NH:27][CH3:28])=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([N:86](C)C)=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH:10]2[CH2:11][N:8]([C:4]3[N:3]=[C:2]([NH:86][C:22]4[CH:23]=[C:24]([CH:29]=[CH:30][CH:21]=4)[C:25]([NH:27][CH3:28])=[O:26])[CH:7]=[CH:6][CH:5]=3)[CH2:9]2)=[CH:14][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 2355164-Amino-N-methylbenzamideHCID 634876Binap, (A+-)-HCID 866852582-Chloro-6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridine

Produkt 1

HCID 67355595
3-(6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide
Ausbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2-chloro-6-(3-(4-fluorophenoxy) azetidin-1-yl)pyridine (500 mg, 1.79 mmoL) and 4-amino-N-methylbenzamide (270 mg, 1.79 mmol) in dimethylacetamide (5 mL, 3 mL/mmol) was added cesium carbonate (873 mg, 2.68 mmol) and the reaction was degassed for 15 min. Pd2(dba)3 (81 mg, 0.089 mmol) and BINAP (55 mg, 0.089 mmol) were added and the reaction was allowed to heat at 120° C. in the microwave. The reaction was quenched with water and extracted with EtOAc (2×50 mL). The organic extracts were washed with brine, dried over sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography to afford 3-(6-(3-(4-fluorophenoxy) azetidin-1-yl)pyridin-2-ylamino)-N-methylbenzamide (61 mg, 13%) as a solid. Observed mass (M+1): 393.1. The following compounds were prepared as described in Example V above using appropriate starting materials.

Aufarbeitung

  1. customthe reaction was degassed for 15 min
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eee1e11f6b46466aa9bba959a9aea0bb
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09334269B2

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