Water → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Temperature

0 °C

A solution of sodium hydride (1.44 g, 60 mmol) in dimethyl formamide/dimethyl sulfoxide (5:1, 120 mL) cooled to 0° C. was treated with a solution of 7-azaindole (4.72 g, 40 mmol) in dimethyl formamide dropwise. The mixture was then stirred at 0° C. for 15 min, then room temperature for 30 min and then recooled to 0° C. After this time, 2-(trimethylsilyl)ethoxymethyl chloride (10.62 mL, 60 mmol) was added dropwise. The mixture was then stirred for 30 min at 0° C. and then warmed to room temperature and stirred for 2 h. The mixture was then poured into water (200 mL) slowly. The aqueous layer was extracted with diethyl ether (2×50 mL). The combined organic layers were then dried over magnesium sulfate, filtered and the filterate concentrated in vacuo. The orange oil was then purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 33% ethyl acetate/hexanes) to afford 1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (10.02 g, 99%) as a pale yellow liquid.

1. waitroom temperature for 30 min
2. customrecooled to 0° C
3. stirringThe mixture was then stirred for 30 min at 0° C.
4. temperaturewarmed to room temperature
5. stirringstirred for 2 h
6. extractionThe aqueous layer was extracted with diethyl ether (2×50 mL)
7. dry with materialThe combined organic layers were then dried over magnesium sulfate
8. filtrationfiltered
9. concentrationthe filterate concentrated in vacuo
10. customThe orange oil was then purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 33% ethyl acetate/hexanes)

ORD record

ord-63a108e44ec64946b29755848551c4db

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222416B2