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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1619359Generated: November 1, 2026

Triethylamine → HCID 58574504, compound

https://huagongshe.com/reaction/1619359

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantTriphenylphosphineHCID 11776—
ReactantTrimethylsilylacetyleneHCID 66111—
ReactantHCID 58574404HCID 58574404—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 58574504HCID 58574504—

Reaction Steps

A solution of 3-bromo-9,10-dihydro-6H-spiro[azepino[2,1-b]quinazoline-8,2′-[1,3]dioxolan]-12(7H)-one (1.74 g, 4.96 mmol, 1 equiv), ethynyltrimethylsilane (972 mg, 9.92 mmol, 2 equiv), Pd(OAc)2 (223.2 mg, 0.992 mmol, 0.2 equiv), PPh3 (1.04 g, 3.96 mmol, 0.8 equiv), CuI (189 mg, 0.992 mmol, 0.2 equiv) and Et3N (1.3 mL) in DMF (50 mL) was stirred in a sealed tube at 70° C. for 3.5 hours. After it was cooled to room temperature, the reaction mixture was diluted with H2O and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The product was obtained by silica gel chromatography purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08772301B2
Source datasetuspto-grants-2014_07
ORD IDord-2887b101e30649c3b5491c507b1e02cd
Source noteuspto-grants-2014_07