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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2173932Generated: October 31, 2026

Dabco → tert-Butyl 4-((5-cyano-1H-benzo[d]imidazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

https://huagongshe.com/reaction/2173932

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDabcoHCID 9237—
Reactant3,4-DiaminobenzonitrileHCID 737285—
Reactanttert-Butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylateHCID 86701482—
SolventEthyl AcetateHCID 8857—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Producttert-Butyl 4-((5-cyano-1H-benzo[d]imidazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylateHCID 178488595—

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of tert-butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (1.3 g, 2.92 mmol), 3,4-diaminobenzonitrile (700 mg, 5.26 mmol) and DABCO (819 mg, 7.30 mmol) in NMP (12 mL) was stirred at 110° C. for overnight. The reaction mixture was then cooled to room temperature, diluted with EtOAc, and washed with water. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified using FCC eluting with heptane/EtOAc(60-80%) to provide the title compound. MS (ESI+) m/z 417.2 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09056874B2
Source datasetuspto-grants-2015_06
ORD IDord-7fafeb1ce76a44ba9ea4d9f433f5b8df
Source noteuspto-grants-2015_06