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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 930532Generated: November 1, 2026

Sodium hydride → HCID 117889759, compound

https://huagongshe.com/reaction/930532

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantCyclopropanemethanolHCID 75644—
ReactantBinap, (A+-)-HCID 634876—
ReactantHCID 117891964HCID 117891964—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
ProductHCID 117889759HCID 11788975933.5%

Reaction Conditions

Temperature70 °C

Reaction Steps

Cyclopropyl methanol (7.4 mg; 0.103 mmol) is dissolved in toluene (1 ml) and added to NaH 60% w/w (8.3 mg; 0.348 mmol). The mixture is stirred at 70° C. for 15 min under a nitrogen atmosphere. Then a mixture of (5-[6-Chloro-1-(1-pyridin-2-yl-ethyl)-1H-imidazo[4,5-c]pyridin-2-yl]-1,3-dimethyl-1H-pyridin-2-one II-21′ (30 mg; 0.079 mmol), BINAP (9.8 mg; 0.016 mmol), Pd2(dba)3 (7.2 mg; 0.008 mmol) is added in toluene (1 ml) and stirred for 2 hours at 100° C. The reaction mixture is evaporated and dissolved in DMF. The mixture is purified using reversed phase column chromatography (Method: prep. HPLC3). The product containing fractions are lyophilized to afford the desired compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09296748B2
Source datasetuspto-grants-2016_03
ORD IDord-5868d8cd47b748fba368fd8e586c7336
Source noteuspto-grants-2016_03