Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 710304Generated: October 29, 2026

Cesium carbonate → tert-Butyl 5-((5-((4,6-dichlorobenzofuran-2-yl)methoxy)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

https://huagongshe.com/reaction/710304

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant4,6-Dichloro-2-(chloromethyl)benzofuranHCID 66726247—
Reactanttert-Butyl 5-((5-hydroxyindolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateHCID 66726286—
SolventDiethyl EtherHCID 3283—
SolventDimethylformamideHCID 6228—
Producttert-Butyl 5-((5-((4,6-dichlorobenzofuran-2-yl)methoxy)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateHCID 8666176241.2%

Reaction Steps

A mixture of the product of Step F (0.05 g; 0.21 mmol) and the product of Step C (0.08 g; 0.21 mmol) and Cs2CO3 (0.07 g; 0.21 mmol) in anhydrous DMF (1 ml) was stirred overnight at room temperature under N2. This was diluted to 10 ml with diethyl ether, washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc 7:3), to give the title compound (0.05 g; 41%) as a brownish syrup. 1H-NMR (CDCl3) 1.44 (m, 15H); 2.95 (tr, 2H, J=8.5 Hz); 3.41 (tr, 2H, J=8.5 Hz); 3.45 (5, 2H); 3.87-4.01 (m, 4H); 4.69 (broad s, 1H); 5.03 (s, 2H); 6.49 (d, 1H, J=8.5 Hz); 6.69 (dd, 1H, J=2.5, 8.5 Hz); 6.79 (s, 2H); 7.23 (s, 1H, J=2.5 Hz); 7.39 (s, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09181182B2
Source datasetuspto-grants-2015_11
ORD IDord-edf48cb64c544a0fa314bb5f31a1c361
Source noteuspto-grants-2015_11