Isobutylamine → Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate

HRID 906187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906187
Br[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]#[N:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:15][CH:16]([CH3:19])[CH2:17][NH2:18].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[C:13]([C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[NH:18][CH2:17][CH:16]([CH3:19])[CH3:15])#[N:14]

Komponenten

8

Edukt 4

HCID 6558IsobutylamineHCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 18374323Ethyl 3-bromo-4-cyanobenzoate

Produkt 1

HCID 67405767Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoateAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 2.08 mmol), 2-methylpropan-1-amine (250 μL, 4.16 mmol), Pd2(dba)3 (96 mg, 5 mol %), Xantphos (120 mg, 10 mol %) and potassium phosphate (959 mg, 4.16 mmol) in dioxane (10 mL) was stirred for overnight at 95° C. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated followed by column chromatography (10% ethyl acetate in hexanes) to give ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 76.7%) as a yellow solid. 1MS (EI) for C14H18N2O2: 247.1 (MH+).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-893de11e4b9e48e6a28b510f3b5248e1
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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