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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2088971Generated: October 30, 2026

1-(Trimethylsilyl)prop-1-yne → 5-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

https://huagongshe.com/reaction/2088971

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-(Trimethylsilyl)prop-1-yneHCID 80363—
ReactantLithium ChlorideHCID 433294—
ReactantPotassium AcetateHCID 517044—
Reactant5-Bromo-3-iodo-4-methylpyridin-2-amineHCID 40151897—
Catalystpalladium(II) acetateHCID 167845—
SolventDimethylformamideHCID 6228—
Product5-Bromo-3,4-dimethyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 67077681—

Reaction Conditions

Temperature90 °C

Reaction Steps

The compound obtained in step 1 of Example 36 (1.8 g) was dissolved in N,N-dimethylformamide (40 ml), and potassium acetate (1.7 g) and lithium chloride (0.3 g) were added. After replacing the atmosphere in the system with nitrogen, palladium acetate (0.13 g) and 1-trimethylsilyl-1-propyne (4.3 ml) were added and the mixture was stirred at 90° C. for three days. The reaction solution was cooled to room temperature and then N,N-dimethylformamide was distilled off. The resulting residue was diluted with ethyl acetate and then washed with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to give the crude title compound (2.4 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08436012B2
Source datasetuspto-grants-2013_05
ORD IDord-2c6d41755b0f471d968288d0cc8b4c4a
Source noteuspto-grants-2013_05