Triethylamine → N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamide

HRID 558142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558142
[F:1][CH:2]([F:6])[C:3](O)=[O:4].[Br:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH:15]([NH2:17])[CH3:16].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[Br:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH:15]([NH:17][C:3](=[O:4])[CH:2]([F:6])[F:1])[CH3:16]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 9788Difluoroacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 570869192-Bromo-4-fluoro-α-methylbenzenemethanamine

Produkt 1

HCID 57445093N-(1-(2-Bromo-4-fluorophenyl)ethyl)-2,2-difluoroacetamideAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Add difluoroacetic acid (777 mg, 8.1 mmol) to a mixture of 1-(2-bromo-4-fluorophenyl)ethanamine (1.18 g, 5.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.55 g, 8.1 mmol), 1-hydroxybenzotriazole hydrate (1.24 g, 8.1 mmol), and triethylamine (2.26 mL, 16.2 mmol) in DCM (20 mL) at 0° C. Stir the mixture at RT overnight. Dilute the mixture with DCM, wash with water and aqueous saturated sodium chloride. Separate the organic layer and dry over sodium sulfate. Filter and concentrate in vacuo. Purify the residue by column chromatography [5% to 50% ethyl acetate in hexanes] to give the title compound (1.06 g, 44%). MS (ES) m/z 296 [M+1]+.

Aufarbeitung

  1. washwash with water and aqueous saturated sodium chloride
  2. customSeparate the organic layer
  3. dry with materialdry over sodium sulfate
  4. filtrationFilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by column chromatography [5% to 50% ethyl acetate in hexanes]

Quellen und Nachweise

ORD-Eintrag
ord-f65d95b124214c7fbf1caddf6f6481ca
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063035B2

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