Dichloromethane → 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-1-[tris(1-methylethyl)silyl]-, methyl ester

Temperature

-78 °C

4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (0.50 g, 1.612 mmol, see Example 1) was dissolved in THF (15 mL) and cooled to −78° C. s-BuLi (2.54 mL, 3.56 mmol) was then added dropwise, and the solution was stirred at −78° C. for 30 minutes. Methyl chloroformate (0.38 mL, 4.98 mmol) was then added as a THF (2 mL) solution, and the reaction was stirred for an additional 30 minutes. The reaction was then quenched with saturated NH4Cl and allowed to warm to room temperature. The reaction was then extracted with DCM (3×50 mL), dried, and filtered to give a crude residue. The crude residue was purified by column chromatography with 5:1 hexane:DCM to give methyl 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.55 g, 91% yield).

1. additionwas then added dropwise
2. stirringthe reaction was stirred for an additional 30 minutes
3. customThe reaction was then quenched with saturated NH4Cl
4. temperatureto warm to room temperature
5. extractionThe reaction was then extracted with DCM (3×50 mL)
6. customdried
7. filtrationfiltered
8. customto give a crude residue
9. customThe crude residue was purified by column chromatography with 5:1 hexane

ORD record

ord-7e555e64f1a341cda778dd344ade840f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841304B2