Triethylamine → N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamide

HRID 2080658

Reaktionsgleichung

Reaktionsgleichung von HRID 2080658
C(N(CC)CC)C.Cl.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](Cl)=[O:16].[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=1[F:26]>C(Cl)(Cl)Cl>[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=2)=[O:16])=[CH:21][C:20]=1[F:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 8218484-Bromo-3-fluoroaniline

Produkt 1

HCID 23145244N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamideAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

2.9 ml of triethylamine and 1.87 g of picolinic acid chloride hydrochloride were added to a chloroform (30 ml) solution of 1 g of 4-bromo-3-fluoroaniline, and stirred at room temperature for 4 hours. The reaction liquid was diluted with chloroform, washed with aqueous saturated sodium bicarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to obtain 1.44 g of the entitled compound as a pale yellow crystal.

Aufarbeitung

  1. customThe reaction liquid
  2. washwashed with aqueous saturated sodium bicarbonate solution and saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated away
  5. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-d0c1e3ecd2c34458b553a72b4096c6c1
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932394B2

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