Potassium Phosphate, Tribasic → 5-(3-Bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile

HRID 1942632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942632
[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:5]=1[C:6]#[N:7].[Br:22][C:23]1[N:27]=[C:26](Cl)[S:25][N:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C.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]>[Br:22][C:23]1[N:27]=[C:26]([C:9]2[CH:10]=[CH:11][C:4]([CH2:3][CH:2]([CH3:1])[CH3:21])=[C:5]([CH:8]=2)[C:6]#[N:7])[S:25][N:24]=1

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27250533-Bromo-5-chloro-1,2,4-thiadiazoleHCID 51358167Benzonitrile, 2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Produkt 1

HCID 669817585-(3-Bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrileAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (D59) (500 mg), 3-bromo-5-chloro-1,2,4-thiadiazole (699 mg) and tripotassium phosphate (1116 mg) in N,N-dimethylformamide (DMF) (6 mL) and water (1.500 mL) stirred under nitrogen was added PdCl2(dppf) (154 mg). The reaction mixture was sealed and heated under microwave at 80° C. for 1 h. After cooling the reaction, the mixture was diluted with ethyl acetate, the organic phase was washed with water, dried and concentrated, the residue was purified by column chromatography to afford 5-(3-bromo-1,2,4-thiadiazol-5-yl)-2-(2-methylpropyl)benzonitrile (D60) (500 mg). δH (CDCl3, 400 MHz): 0.99 (6H, d), 2.04 (1H, m), 2.80 (2H, d), 7.46 (1H, d), 8.05 (1H, dd), 8.22 (1H, d). MS (ES): C13H12BrN3S requires 321. found 322.0 (M+H+).

Aufarbeitung

  1. customThe reaction mixture was sealed
  2. temperatureAfter cooling
  3. customthe reaction
  4. washthe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8ec5e75776284223949eebea1236fcc3
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389508B2

Notizen zur Reaktion

Wird geladen…