Sodium Carbonate → N-[(3,5-difluoro-3'-nitro-4-biphenylyl)methyl]-2,3-dihydro-1H-inden-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Benzene, 1-bromo-3-nitro-	HCID 11457	—
Reactant	{4-[(2,3-dihydro-1H-inden-2-ylamino)methyl]-3,5-difluorophenyl}boronic acid	HCID 59316459	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-[(3,5-difluoro-3'-nitro-4-biphenylyl)methyl]-2,3-dihydro-1H-inden-2-amine	HCID 67160310	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of {4-[(2,3-dihydro-1H-inden-2-ylamino)methyl]-3,5-difluoro-phenyl}boronic acid (740 mg, 2.44 mmol; Ex V-22), 3-bromonitrobenzene (495 mg, 2.44 mmol), PdCl2(dppf)2 (100 mg, 0.12 mmol) and Na2CO3 (4.90 mL, 2.0 M (aq)) in DME (10 mL) was stirred at 80° C. for 45 min. The mixture was diluted with EtOAc then filtered through a pad of Celite and silica gel. The filtrate was washed with H2O and brine, dried over Na2SO4 then concentrated to give N-[(3,5-difluoro-3′-nitro-4-biphenylyl)methyl]-2,3-dihydro-1H-inden-2-amine as a tan glass. LC/MS (method A) 0.62 min, (m/z) 381 (70%), 382 (100%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08822518B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-53a5403519d04d5e939b86c3c3f282f8
Source note	uspto-grants-2014_09