4-(Bromoacetyl)pyridine hydrobromide → 4-(4-Pyridin-4-yl-thiazol-2-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester

HRID 221375

Reaktionsgleichung

Reaktionsgleichung von HRID 221375
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([O:25][CH2:26][C:27](=[S:29])[NH2:28])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CO.CCOC(C)=O>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][CH:22]([O:25][CH2:26][C:27]2[S:29][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=3)[N:28]=2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Komponenten

5

Edukt 2

HCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 45496681Tert-butyl 4-(carbamothioylmethoxy)piperidine-1-carboxylate

Produkt 1

HCID 579544514-(4-Pyridin-4-yl-thiazol-2-ylmethoxy)piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-1-pyridin-4-yl-ethanone hydrobromide (35 mg, 1241 mol) and 4-thiocarbamoylmethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 18, 34 mg, 124 μmol) in methanol (2 ml) was heated at 60° C. for 1.5 h. The reaction mixture was diluted with EtOAc (60 ml), washed with saturated aqueous NaHCO3 (15 ml) and brine (15 ml) then dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (EtOAc) to afford the title compound: RT=2.95 ml, m/z (ES+)=376.1 [M+H]+.

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 (15 ml) and brine (15 ml)
  2. dry with materialthen dried (MgSO4)
  3. customThe solvent was removed
  4. customthe residue purified by flash chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-af4f12460c324f09932ce5267922013d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207147B2

Verknüpfte Notizen

Wird geladen…