6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid methyl ester → 6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid

HRID 31986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31986
C[O:2][C:3]([C:5]1[C:18]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[CH3:27])=[C:17]([F:28])[C:8]2[N:9]=[CH:10][N:11]([CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])[C:7]=2[CH:6]=1)=[O:4]>C1COCC1.CO.[OH-].[Na+]>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:18]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]3[N:11]([CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])[CH:10]=[N:9][C:8]=3[C:17]=2[F:28])=[C:21]([CH3:27])[CH:22]=1

Komponenten

4

Edukt 1

HCID 668851756-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid methyl ester

Produkt 1

HCID 211142136-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798Sodium HydroxideLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid methyl ester 9b is dissolved in 1:1 THF/MeOH (10 mL) and 1 N NaOH solution (2.3 mL) is added. After 5 hours, the organic solvents are removed under reduced pressure and the residue diluted with water and 100 mL 1:1 THF:ethyl acetate. The layers are separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure to afford 0.39 g (100%) clean desired product as a light yellow solid.

Aufarbeitung

  1. additionis added
  2. customthe organic solvents are removed under reduced pressure
  3. additionthe residue diluted with water and 100 mL 1:1 THF
  4. customThe layers are separated
  5. extractionthe aqueous layer extracted with ethyl acetate
  6. dry with materialThe combined organic extracts are dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7790d327c83e457cab45910cb29d5468
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425637B2

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