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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 720138Generated: October 29, 2026

Tributylvinyltin → (6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/720138

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylvinyltinHCID 81998—
Reactant8-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl esterHCID 136181612—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
Product(6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl esterHCID 13614170884%

Reaction Steps

Under an argon atmosphere, Intermediate 147(d) of Example 147 (0.250 g, 0.661 mmol), tributyl-vinyl-tin (0.420 g, 1.32 mmol) and tetrakis(triphenylphosphine)palladium(0) (38 mg, 0.033 mmol) in anhydrous N,N-dimethylformamide (5 mL) were heated at 85° C. for 16 hours. The reaction was filtered through a thin pack of diatomaceous earth, and the filtrate concentrated in vacuo. Silica gel chromatography (eluted with 1:4 ethyl acetate: dichloromethane) afforded the title compound (0.18 g, 0.552 mmol) as a yellow powder in 84% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07132533B2
Source datasetuspto-grants-2006_11
ORD IDord-1bc70eb86a614e2bbd29e688d9455911
Source noteuspto-grants-2006_11