反応 #1182919

反応方程式

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

収率 35.2%

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

収率 35.2%

溶媒

DCM

EtOAc H2O

DMF

反応条件

後処理

1. 1
   抽出The aqueous layer was extracted with EtOAc
2. 2
   乾燥The combined organic layers were dried (Na2SO4)
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他to give crude, N-Boc-protected product
6. 6
   workup.STIRRINGThis mixture was stirred for 30 minutes
7. 7
   濃縮concentrated
8. 8
   その他The residue was purified by silica gel chromatography
9. 9
   洗浄eluting with DCM/MeOH/NH4OH (10:1:0.1)

実験手順

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.

出典