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Diisopropylethylamine → Thiophene-3-carboxylic acid n'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-n'-isopropyl-hydrazid

HRID 2250891
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2250891
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH:14]([NH:17][NH:18][C:19]([C:21]1[CH:25]=[CH:24][S:23][CH:22]=1)=[O:20])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([N:17]([CH:14]([CH3:16])[CH3:15])[NH:18][C:19]([C:21]1[CH:25]=[CH:24][S:23][CH:22]=1)=[O:20])=[O:8]
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Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 3028732-(2-Bromo-4-fluorophenoxy)acetic acidHCID 2733179PyBroPHCID 59642162thiophene-3-carboxylic acid N'-isopropyl-hydrazide

Produkt 1

HCID 58689906Thiophene-3-carboxylic acid n'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-n'-isopropyl-hydrazidAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (2-bromo-4-fluoro-phenoxy)-acetic acid (226 mg, 0.91 mmol) and thiophene-3-carboxylic acid N′-isopropyl-hydrazide (200 mg, 1.09 mmol) in DMF (5 ml) was treated with diisopropylethyl amine (0.40 mL, 2.28 mmol) and PyBroP (636 mg, 1.37 mmol) at room temperature overnight. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was washed with brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient to afford the product as a solid (251 mg, 66%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-e9aae6b215af4c9198b145a55baffc76
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07317125B2

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