Hydrochloric Acid → [2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]methylamine

HRID 734870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734870
C=O.[C:3]([BH3-])#[N:4].[Na+].[Br:7][C:8]1[C:13](N)=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][N:9]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CC(O)=O>[Br:7][C:8]1[C:13]([CH2:3][NH2:4])=[CH:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:10][N:9]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 859697042-Bromo-5-(4-chloro-phenyl)-pyridin-3-ylamine

Produkt 1

HCID 86601137[2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]methylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.32 mL (17.63 mmol) of formalin solution (37% in water) and 443 mg (7.05 mmol) of sodium cyanoborohydride were added to a solution of 0.50 g (1.76 mmol) of 2-bromo-5-(4-chlorophenyl)pyridin-3-ylamine (Example 16.1c) in 20 mL of acetonitrile, the mixture was acidified to pH 4 with HOAc, and stirred for 16 hours at RT. The reaction mixture was acidified with 4M aqueous HCl and stirred for 1 hour at RT. It was made alkaline with sat. aqueous sodium carbonate solution and the aqueous phase was exhaustively extracted with DCM. The combined organic phases were dried over magnesium sulfate and evaporated down in vacuo. The residue was purified by chromatography (silica gel, gradient PE/DCM 50:50→100:0). Yield: 0.24 g (46% of theoretical); C12H10BrClN2 (M=297.578); calc.: molpeak (M+H)+: 297/299/301 (BrCl); found: molpeak (M+H)+:297/299/301 (BrCl); HPLC-MS: 6.09 minutes (method B).

Aufarbeitung

  1. stirringstirred for 1 hour at RT
  2. extractionthe aqueous phase was exhaustively extracted with DCM
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customevaporated down in vacuo
  5. customThe residue was purified by chromatography (silica gel, gradient PE/DCM 50:50→100:0)
  6. custom6.09 minutes (method B)

Quellen und Nachweise

ORD-Eintrag
ord-9c9580a458284edb993b0882e5151c77
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592358B2

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