Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 74687Generated: October 26, 2026

Diisopropylethylamine → 1-[6'-chloro-4'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

https://huagongshe.com/reaction/74687

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantBms-973013HCID 22293182—
Reactant(2,6-Dichloro-pyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanoneHCID 58386613—
SolventDimethylformamideHCID 6228—
Product1-[6'-chloro-4'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-oneHCID 58386568—

Reaction Steps

0.74 g (3.4 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 1.0 g (3.2 mmol) (2,6-dichloro-pyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 0.65 mL (3.8 mmol) DIPEA in 10 mL DMF were stirred for 2 h at RT. Then the reaction mixture was evaporated down, the residue was mixed with water and stirred for 30 min at RT. The precipitated solid was suction filtered, stirred with diisopropylether and isopropanol and suction filtered again. After drying the crude product was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829006B2
Source datasetuspto-grants-2014_09
ORD IDord-823ddf6bf1f54c0c800a71b1bba1c675
Source noteuspto-grants-2014_09