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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 38813Generated: October 26, 2026

Potassium Phosphate, Tribasic → 6-(1H-Indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-4-[5-(4-morpholinylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazole

https://huagongshe.com/reaction/38813

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant1H-Indole-4-boronic acid, pinacol esterHCID 11322471—
Reactant6-Bromo-1-[(4-methylphenyl)sulfonyl]-4-[5-(4-morpholinylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazoleHCID 66695822—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product6-(1H-Indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-4-[5-(4-morpholinylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazoleHCID 6677660229.8%

Reaction Conditions

Temperature100 °C

Reaction Steps

A stirred mixture of 6-bromo-1-[(4-methylphenyl)sulfonyl]-4-[5-(4-morpholinylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazole (75 mg, 0.145 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (52.8 mg, 0.217 mmol), 1,1′-bis(diphenylphosphino)-ferrocene palladium dichloride (5.29 mg, 7.23 μmol) and tripotassium phosphate (92 mg, 0.434 mmol) in 1,4-dioxane (2 ml) and water (0.2 ml) was heated at 100° C. in the microwave (Biotage initiator) for 30 mins. The mixture was poured into water (40 ml) and extracted into ethyl acetate (2×30 ml). The combined extracts were washed with water (30 ml), dried (frit) and evaporated. The residual solid was purified on a silica (5 g) cartridge using ether and ethyl acetate/ether (2:1) as the eluent. The appropriate fractions were evaporated to dryness to give the title compound as a cream coloured solid (24 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08524751B2
Source datasetuspto-grants-2013_09
ORD IDord-8c36e0612faa450d8a35ad3ce46c7a8c
Source noteuspto-grants-2013_09