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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 75248Generated: October 25, 2026

Benzodiazepine → N-methylbenzodiazepine

https://huagongshe.com/reaction/75248

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzodiazepineHCID 134664—
ReactantMethyl iodide sodium hydrideHCID 23686416—
CatalystPalladiumHCID 23938—
ProductN-methylbenzodiazepineHCID 12543525—

Reaction Steps

The bromide 20 available from references 9 and 10 was reacted with trimethylsilyacetylene in the presence of a palladium catalyst to provide trimethylsilyl analog 52. This product was methylated with methyl iodide/sodium hydride to give the N-methyl benzodiazepine 54 (XLi 351). This was subjected to fluoride-mediated desilation to furnish 53 (XLi 350) and 55 (XLi 352).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835424B2
Source datasetuspto-grants-2014_09
ORD IDord-1b3beb3ba5df4868b8f6774c959dce1a
Source noteuspto-grants-2014_09