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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 75226Generated: November 2, 2026

Dimethylformamide → 5-Chloro-4(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepine-2yl)nicotinonitrile tris(trifluoroacetate)

https://huagongshe.com/reaction/75226

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantHCID 86762737HCID 86762737—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
Product5-Chloro-4(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepine-2yl)nicotinonitrile tris(trifluoroacetate)HCID 8676273613%

Reaction Conditions

Temperature175 °C

Reaction Steps

2-(3,5-Dichloropyridin-4-yl)-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4′,3′-f]azepine bis(trifluoroacetate) (200 mg, 0.3 mmol), zinc cyanide (231 mg, 1.97 mmol), and tetrakis-(triphenylphosphine)palladium(0) (190 mg, 0.16 mmol) were stirred in N,N-dimethylformamide and degassed for 10 minutes by bubbling with nitrogen gas. The mixture was heated in a microwave for 20 minutes at 175° C. Purification by preparative LCMS gave the desired product (25 mg, 13%). 1H NMR (DMSO-d6): δ 9.20 (d, 2H), 8.60 (m, 1H), 8.0 (m, 1H), 7.65 (m, 1H), 6.90 (m, 1H). LC/MS: 372 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835423B2
Source datasetuspto-grants-2014_09
ORD IDord-3a62f0f0017841d2a965ece83ffbd761
Source noteuspto-grants-2014_09