Reaktion #1182919

Reaktionsgleichung

TFA

2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol

tert-butyl 2-bromoethylcarbamate

t-butylammonium iodide

cesium hydroxide hydrate

→

desired product

Ausbeute 35.2%

2-(2-(7-(2-methoxyethoxy)imidazo[1.2-a]pyridin-3-yl)quinolin-8-yloxy)ethanamine

Ausbeute 35.2%

Lösungsmittel

DCM

EtOAc H2O

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous layer was extracted with EtOAc
2. 2
   TrocknenThe combined organic layers were dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give crude, N-Boc-protected product
6. 6
   workup.STIRRINGThis mixture was stirred for 30 minutes
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by silica gel chromatography
9. 9
   Wascheneluting with DCM/MeOH/NH4OH (10:1:0.1)

Vorschrift

To 2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol (50 mg, 0.15 mmol) in DMF (3 mL) was added 4 angstrom molecular sieves (2 g), tert-butyl 2-bromoethylcarbamate (40 mg, 0.18 mmol), t-butylammonium iodide (3 mg) and cesium hydroxide hydrate (50 mg, 0.30 mmol). The reaction mixture was stirred overnight, then dilute with EtOAc/H2O (10 mL/10 mL). The aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated to give crude, N-Boc-protected product, to which was added DCM (1 mL) and TFA (1 mL). This mixture was stirred for 30 minutes and then concentrated. The residue was purified by silica gel chromatography, eluting with DCM/MeOH/NH4OH (10:1:0.1) to provide the desired product (20 mg). APCI (+) m/z 379.2 (M+1) detected.

Quelle