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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2267544Generated: October 26, 2026

Cesium carbonate → 3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide

https://huagongshe.com/reaction/2267544

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant[3-(Hydroxymethyl)phenyl]boronic acidHCID 2734662—
Reactant3-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamideHCID 11620053—
Reactant5-bromo-3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamideHCID 59003361—
CatalystHCID 178418397HCID 178418397—
Product3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-5-[3-(hydroxymethyl)phenyl]-1H-indole-7-carboxamideHCID 11605713—

Reaction Steps

The title compound was prepared following the general procedure described in intermediate 16. Thus, 5-bromo-3-(1-{[3-(dimethylamino)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (150 mg, 0.32 mmol), [3-(hydroxymethyl)phenyl]boronic acid (195 mg, 1.27 mmol), Pd(PPh3)4 (31 mg, 10%) and cesium carbonate (220 mg, 0.64 mmol) were reacted to form the desired product which was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to yield the desired product (230.0 mg, 36%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07858796B2
Source datasetuspto-grants-2010_12
ORD IDord-bd7e866203894a1a9680b38e2b74d4b7
Source noteuspto-grants-2010_12