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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 413347Generated: October 28, 2026

Diisopropylethylamine → 4-[[2-(2-bromophenyl)-1,5,6,7,8,8a-hexahydro-1-oxoimidazo[1,5-a]pyridin-3(2H)-ylidene]amino]-3-hydroxybenzonitrile

https://huagongshe.com/reaction/413347

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantTetrabutylammonium FluorideHCID 2724141—
ReactantN-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)carbodiimideHCID 12043083—
ReactantMethyl Pipecolinate HydrochlorideHCID 13246231—
SolventMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
Product4-[[2-(2-bromophenyl)-1,5,6,7,8,8a-hexahydro-1-oxoimidazo[1,5-a]pyridin-3(2H)-ylidene]amino]-3-hydroxybenzonitrileHCID 984529275.2%

Reaction Steps

The standard procedure was followed using N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)carbodiimide (106 mg, 0.25 mmol), diisopropylethylamine (71 μL, 0.28 mmol), methyl pipecolinate hydro chloride (50 mg, 0.28 mmol) and TBAF (0.30 mL, 0.30 mmol) in THF (2.5 mL) and methanol (0.1 mL) to give 80 mg (75%) of 4-[[2-(2-bromophenyl)-1,5,6,7,8,8a-hexahydro-1-oxoimidazo[1,5-a]pyridin-3(2H)-ylidene]amino]-3-hydroxybenzonitrile as a tan powder. MS (EI) m/e 425 (100(M+)).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06566387B1
Source datasetuspto-grants-2003_05
ORD IDord-b2de64230ac1478ab4dbc44434fc63e5
Source noteuspto-grants-2003_05