1,2-Dimethoxyethane → 2-Amino-5-{3-[(E)-2-cyclopropylvinyl]phenyl}-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dimethoxyethane	HCID 8071	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	(E)-2-Cyclopropylethylene-1-boronic acid, pinacol ester	HCID 16217940	—
Reactant	2-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one	HCID 59790307	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Product	2-Amino-5-{3-[(E)-2-cyclopropylvinyl]phenyl}-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one	HCID 59790344	68.5%

Reaction Steps

A mixture of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (150 g, 0.36 mmol), dimethoxyethane, 2-[(E)-2-cyclopropylvinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (105 mg) and Na2CO3 (2 M, 2.5 mL) was degassed under argon for 5 minutes and treated with tetrakis(triphenylphosphine)palladium(0) (21 mg, 0.018 mmol). The reaction mixture was stirred for 15 hour, poured into water and extracted with ethyl acetate. The extracts were combined, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by ICSO (EtOAc/MeOH 10/1) gave the title product as a white solid (98 mg), identified by NMR and mass spectral analyses.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07423158B2
Source dataset	uspto-grants-2008_09
ORD ID	ord-96d739d209104ecb91a497c62837aa7f
Source note	uspto-grants-2008_09