Reaktion #341970

ord-c1053629fc4c4425bb2d19c3bb305c4c

Reaktionsgleichung

CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
Sodium triacetoxyl-borohydride
Nc1cncc(Br)c1
5-bromo-pyridine-3-amine
COc1ccc(C=O)cc1OC1CCCC1
3-cyclopentyloxy-4-methoxy-benzaldehyde
CC(=O)O
HOAc
COc1ccc(CNc2cncc(Br)c2)cc1OC1CCCC1
5-bromo-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyridin-3-amine
Ausbeute 93.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added
  2. 2
    WaschenThe organic phase was washed with water
  3. 3
    Trocknendried over sodium sulfate
  4. 4
    SonstigeThe solvent was removed by under reduced pressure

Vorschrift

Sodium triacetoxyl-borohydride (245 mg, 1.16 mmol) was added to the solution of 5-bromo-pyridine-3-amine (100 mg, 0.57 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (127 mg, 0.57 mmol) in 10 ml of 1,2-dichloroethtane (DCE), of HOAc (66 μL, 2 eq. 1.16 mmol) was added, the mixture was stirred overnight at room temperature, followed by addition of 15 ml of DCE. The organic phase was washed with water, and dried over sodium sulfate. The solvent was removed by under reduced pressure to give 200 mg of crude 5-bromo-N-(3-(cyclopentyloxy)-4-methoxybenzyl)pyridin-3-amine, which was used for the next step without further purification.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07875622B2uspto-grants-2011_01