Hydrochloric Acid → 4-(2-Amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid

HRID 595941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595941
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1.[Li+].[OH-].Cl.CCOC(C)=O>C1COCC1.CO>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 118045477Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate

Produkt 1

HCID 1180467884-(2-Amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate (1.9 g, 5.84 mmol) in THF (19.48 mL) and MeOH (9.74 mL, Ratio: 1.000) was added LiOH (1 M aqueous solutionueous solution) (10.52 mL, 10.52 mmol). The reaction mixture was stirred for 5 h. After 1N HCl (1.9 mL) was added up to pH 5, the reaction mixture was worked up with EtOAc, the organic layer was dried over Na2SO4, filtered off and concentrated in vacuo. The crude 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid was used for the next step without further purification. LCMS (m/z): 311.1/313.1 (MH+), 0.5 min.

Aufarbeitung

  1. dry with materialthe organic layer was dried over Na2SO4
  2. filtrationfiltered off
  3. concentrationconcentrated in vacuo
  4. customThe crude 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid was used for the next step without further purification
  5. custom311.1/313.1 (MH+), 0.5 min.

Quellen und Nachweise

ORD-Eintrag
ord-fa4c0f59979c4c3fbde172247a9d4431
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242996B2

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