Sodium Hydroxide → [6-Methoxy-3-pyridinyl]methylamino-N-[4-(1-propynyl)-3-(trifluoromethyl)phenyl]benzamide

HRID 8900

Reaktionsgleichung

Reaktionsgleichung von HRID 8900
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=2)=[O:14])=[CH:5][CH:4]=1.[CH2:31]([Sn](CCCC)(CCCC)C#CC)[CH2:32][CH2:33]C.[OH-].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:31]#[C:32][CH3:33])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=2)=[O:14])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 99130292-[[6-Methoxy-3-pyridinyl]methyl]amino-N-[4-bromo-3-(trifluoromethyl)phenyl]benzamide

Produkt 1

HCID 9980607[6-Methoxy-3-pyridinyl]methylamino-N-[4-(1-propynyl)-3-(trifluoromethyl)phenyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A stirred solution of 2-[[6-methoxy-3-pyridinyl]methyl]amino-N-[4-bromo-3-(trifluoromethyl)-phenyl]benzamide (Reference Example 1; 3.98 g, 8.3 mmol) in dry toluene (200 mL) is purged with argon for 20 minutes at 25° C. Tributyl-1-propynylstannane (4.1 g of 80%, 9.96 mmol) and tetrakis(triphenylphosphine)palladium (0) (260 mg) are then added and the resulting mixture is heated at 100° C. for 17 hours under an argon atmosphere. The mixture is then cooled, treated with an aqueous solution of sodium hydroxide (85 mL of 0.1 M) and purged with air for 2 hours. The resulting mixture is extracted with ethyl acetate (3×100 mL). The organic phase is sequentially washed with water (2×40 mL) and saturated aqueous sodium chloride (1×40 mL), dried (Na2SO4), filtered and the solvent is evaporated under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 33% ethyl acetate in hexane and recrystallised from diethylether-hexane to give the title compound as a pale-yellow crystalline solid; m.p. 123–124° C.

Aufarbeitung

  1. temperatureThe mixture is then cooled
  2. custompurged with air for 2 hours
  3. extractionThe resulting mixture is extracted with ethyl acetate (3×100 mL)
  4. washThe organic phase is sequentially washed with water (2×40 mL) and saturated aqueous sodium chloride (1×40 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated under reduced pressure
  8. customto yield the crude product which
  9. customis purified by column chromatography on silica gel, eluent 33% ethyl acetate in hexane
  10. customrecrystallised from diethylether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-eb3583fec4e14b0cba6036c1e267daa2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091224B2

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