1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 1-[tris(1-methylethyl)silyl]- synthesis

Yield:858117-08-5 36%

Reaction Conditions:

with sodium hydride in tetrahydrofuran at 20; for 2 h;

Steps:

6.2

Step 2-Preparation of 1-triisopropylsilanyl-1H-pyrrolo[2,3-h]pyridine-3-carbaldehyde (10)To 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde (9, 4.05 g, 27.71 mmol) in tetrahydrofuran (30.0 mL) were added sodium hydride (60% in mineral oil, 1.5 g, 38 mmol) and triisopropylsilyl chloride (8.0 mL, 38 mmol) under an atmosphere of nitrogen. The reaction was stirred for 2 hours at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 10% ethyl acetate in hexane to give the compound (10, 3.0 g, 36%). MS (ESI)[M+H⁺]⁺=303.

References:

US2008/167338,2008,A1 Location in patent:Page/Page column 35-36