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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2174104Generated: October 30, 2026

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

https://huagongshe.com/reaction/2174104

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDabcoHCID 9237—
Reactant3-Amino-4-hydroxybenzonitrileHCID 271258—
Reactanttert-Butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylateHCID 86701482—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Producttert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylateHCID 86701743—

Reaction Steps

A solution of tert-butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 20-A) (0.720 g, 1.617 mmol) and 3-amino-4-hydroxybenzonitrile (0.325 g, 2.426 mmol) and DABCO (0.544 g, 4.85 mmol) in NMP (1.62 ml) was stirred at 100° C. for 16 hrs. The reaction mixture was cooled and loaded onto silica gel to purify via FCC eluting with Heptane/AcOEt:100/0 to 0/100 to obtain the title compound. MS (ESI+) m/z 418.34 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09056874B2
Source datasetuspto-grants-2015_06
ORD IDord-dd5aef5fa38948db94189ec498604d37
Source noteuspto-grants-2015_06