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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1481786Generated: October 31, 2026

Potassium Fluoride → HCID 71284878, compound

https://huagongshe.com/reaction/1481786

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium FluorideHCID 522689—
ReactantTri-tert-butylphosphine tetrafluoroborateHCID 2734635—
Reactant1-Methyl-1H-indole-5-boronic acidHCID 2759867—
ReactantBenzyl 2,4-bis(benzyloxy)-6-bromo-5-hydroxynicotinateHCID 89421752—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTetrahydrofuranHCID 8028—
ProductHCID 71284878HCID 7128487896%

Reaction Conditions

Temperature60 °C

Reaction Steps

A mixture of benzyl 2,4-bis(benzyloxy)-6-bromo-5-hydroxynicotinate (0.23 g, 0.44 mol), 1-methyl-1H-indol-5-ylboronic acid (90 mg, 0.51 mmol), Pd2(dba)3 (20 mg, 0.022 mmol), tri-tert-butylphosphonium tetrafluoroborate (13 mg, 0.044 mmol) and KF (0.26 g, 4.4 mmol) in THF (2.0 mL) was stirred at 60° C. overnight under an Ar atmosphere. The mixture was filtered. The filtrate was evaporated and purified by silica chromatography (2-30% ethyl acetate in hexanes) to give benzyl 2,4-bis(benzyloxy)-5-hydroxy-6-(1-methyl-1H-indol-5-yl)nicotinate (0.24 g, 96%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09409905B2
Source datasetuspto-grants-2016_08
ORD IDord-a7cf1e6d735d4a3a8377175a7973dad5
Source noteuspto-grants-2016_08