Dichloromethane → 4-[3-(2-chloro-phenyl)-indole-1-sulfonyl]-N-(4-fluoro-benzyl)-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Chlorophenylboronic acid	HCID 2734322	—
Reactant	N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide	HCID 58975061	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Water ethylacetate	HCID 22728543	—
Product	4-[3-(2-chloro-phenyl)-indole-1-sulfonyl]-N-(4-fluoro-benzyl)-benzamide	HCID 58975089	60%

Reaction Steps

Add N-(4-Fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (268 mg, 0.0.50 mmol), 2-chlorophenylboronic acid (78.2 mg, 0.50 mmol), PdCl2(dppf).CH2Cl2 (41 mg, 0.05 mmol) and 2M Na2CO3 (0.55 mL, 1.1 mmol) respectively to DMF (15.0 mL) at ambient temperature under N2. Heat the reaction to 100° C. for 16 h. Cool the reaction to ambient temperature and pour into a H2O-EtOAc mixture (200 mL/100 mL). Separate the EtOAc, extract several times with H2O and wash with brine. Dry (MgSO4), filter and evaporate the filtrate. Purify the crude material on silica gel using a gradient hexane-EtOAc system to give 0.155 g (60% yield) of 4-[3-(2-chloro-phenyl)-indole-1-sulfonyl]-N-(4-fluoro-benzyl)-benzamide: Mass spectrum (m/e) M−1) 517.0787.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595339B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-3218a5097b5a4819b5feb9387d19f51f
Source note	uspto-grants-2009_09