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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 872355Generated: October 30, 2026

Dimethylformamide → (1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

https://huagongshe.com/reaction/872355

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium CarbonateHCID 10340—
Reactant2-Benzyloxy-3-bromopyridineHCID 14712456—
Reactant(1-{4-[3-Phenyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl esterHCID 66665620—
Solvent1,4-DioxaneHCID 31275—
Product(1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl esterHCID 66665949—

Reaction Conditions

Temperature110 °C

Reaction Steps

To the crude DMF solution of the boronate from Step 1 was added 2-benzyloxy-3-bromopyridine (0.25 g), aqueous sodium carbonate solution (2M, 2.8 mL) and dioxane (4 mL) and the mixture placed under argon. [1,1-bis-(diphenylphosphino)-ferrocene]-dichloropalladium-dichlormethane-complex (0.070 mg) was added and the mixture heated at 110° C. under microwave irradiation for 30 minutes. On cooling the mixture was partitioned between DCM and water and extracted. The organic portion was washed with brine, dried and concentrated in vacuo. Purification was achieved by chromatography on silica gel to give the title compound (138 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08975265B2
Source datasetuspto-grants-2015_03
ORD IDord-f68346fadb04410eb661446e52b9d0fc
Source noteuspto-grants-2015_03