Boron Trichloride → 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylic acid

HRID 1058681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058681
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([O:17]C)=[O:16])=[C:13]([CH3:19])[NH:12][C:11]3[CH2:20][CH2:21][C:22](=[O:23])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].B(Cl)(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]3[CH2:20][CH2:21][C:22](=[O:23])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

4

Edukt 2

HCID 25135Boron TrichlorideHCID 11383413methyl 4-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylate

Produkt 1

HCID 98639534-(3-bromo-4-fluorophenyl)-2-methyl-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylic acidAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A suspension of the product from Example 10A (1.90 g, 5.0 mmol) in methylene chloride (10 mL) at 5° C. under nitrogen was treated with 1M boron trichloride in methylene chloride (40 mL), stirred overnight, quenched in ice water (100 mL) and ethyl acetate (30 mL), and the aqueous drained off. The suspension of the product in ethyl acetate was filtered, the filter cake was washed with ethyl acetate and dried to provide 1.26 g of the title compound as an orange-pink solid.

Aufarbeitung

  1. customquenched in ice water (100 mL)
  2. additionThe suspension of the product in ethyl acetate
  3. filtrationwas filtered
  4. washthe filter cake was washed with ethyl acetate
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-866e2239ebd042219c80577e39461d63
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518279B2

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