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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 527934Generated: November 1, 2026

Triethylamine → HCID 68027531, compound

https://huagongshe.com/reaction/527934

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantTriphenylphosphineHCID 11776—
ReactantTrimethylsilylacetyleneHCID 66111—
ReactantHCID 66765983HCID 66765983—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 68027531HCID 68027531—

Reaction Conditions

Temperature90 °C

Reaction Steps

Under N2, a mixture of (R)—N-(1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)-5-bromo-N-methylpyridin-2-amine (0.22 g, 0.58 mmol), ethynyltrimethylsilane (0.22 mL, 1.6 mmol), Et3N (0.24 mL, 1.5 mmol), CuI (5.0 mg, 0.03 mmol), PdCl2(PPh3)2 (8.0 mg, 0.01 mmol) and PPh3 (3.0 mg, 0.01 mmol) in DMF (3.0 mL) was stirred at 90° C. for 4 h. The reaction was then cooled to ambient temperature, diluted with water (3 mL), extracted with ethyl acetate (2×10 mL). The combined extracts was washed with brine (2×6 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel to give the titled compound. MS (m/z): 295 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09346810B2
Source datasetuspto-grants-2016_05
ORD IDord-d6e48787ee8e4a5c807b4e80b4e47443
Source noteuspto-grants-2016_05