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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1359365Generated: October 31, 2026

Ammonia → HCID 69758723, compound

https://huagongshe.com/reaction/1359365

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantTriethylamineHCID 8471—
Reactant(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 946095—
ReactantHCID 69758739HCID 69758739—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
SolventDimethylformamideHCID 6228—
ProductHCID 69758723HCID 6975872352.2%

Reaction Conditions

Temperature75 °C

Reaction Steps

A mixture of 510 mg of 2-benzyl-6-(cis-3,4-dimethoxypyrrolidine-1-yl)-3-iodopyridine, 200 mg of (3R)-3-ethynyl-3-quinuclidinol, 139 mg of tetrakis (triphenylphosphine) palladium (0), 11 mg of cuprous iodide, 0.50 ml of triethylamine and 5.0 ml of N,N-dimethylformamide was heated under stirring at 75° C. for 2 hours in a nitrogen atmosphere. The reaction solution was poured into aqueous dilute ammonia and extracted with ethyl acetate. The extract was washed with brine and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (1:1) and then with ethyl acetate/methanol (15:1), to give 281 mg of the target compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06599917B1
Source datasetuspto-grants-2003_07
ORD IDord-daf94c57a2dd47dd8fec13f7274e5c94
Source noteuspto-grants-2003_07