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

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	[3-(Hydroxymethyl)phenyl]boronic acid	HCID 2734662	—
Reactant	3-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide	HCID 11620053	—
Reactant	5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide	HCID 59003300	—
Catalyst	HCID 178418397	HCID 178418397	—
Product	5-[3-(hydroxymethyl)phenyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide	HCID 11613367	—

Reaction Steps

The title compound was prepared following the general procedure for intermediate 16. Thus, 5-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (150 mg, 0.30 mmol), [3-(hydroxymethyl)phenyl]boronic acid (188 mg, 1.20 mmol), Pd(PPh3)4 (30 mg, 10%) and cesium carbonate (200 mg, 0.60 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 (280 mg, 44%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07858796B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-7164a11be59b45069eb2d18b0b64fa53
Source note	uspto-grants-2010_12