Water → HCID 66591283, Verbindung

HRID 1092276

Reaktionsgleichung

Reaktionsgleichung von HRID 1092276
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.CN[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.O.[CH3:21][N:22](C)C=O>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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[C:13]([CH2:21][NH2:22])[CH:12]=[CH:11][CH:16]=2)=[N:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 693532,5-DibromopyridineHCID 23558980[3-(Methylamino)phenyl]boronic acid

Produkt 1

HCID 66591283HCID 66591283, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2.2 g (9.5 mmol, 1.2 eq) of 2,5-dibromopyridine are dissolved in 3 mL of an 8/2 mixture of dimethylformamide/2M potassium phosphate. 1.2 g (7.9 mmol, 1 eq) of N-methyl-3-aminophenylboronic acid are added along with 456 mg (0.39 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium. The mixture is stirred for 3 hours at 90° C. The reaction is stopped by adding 30 mL of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and the residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate). 1.07 g of [3-(5-bromopyrid-2-yl)phenyl]methylamine are obtained. Yield 52%.

Aufarbeitung

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5462fe44302a4c3a93cb4fa2f07ab868
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129416B2

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