Potassium Carbonate → 5-[3-[3-(3,4-dihydro-1H-isoquinolin-2-yl)-2-hydroxypropoxy]phenyl]-1,3-dihydrobenzimidazol-2-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-Bromo-1,3-dihydro-2H-benzimidazol-2-one	HCID 12228060	—
Reactant	1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-ol	HCID 86729236	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane--water (1/1)	HCID 21886435	—
Product	5-[3-[3-(3,4-dihydro-1H-isoquinolin-2-yl)-2-hydroxypropoxy]phenyl]-1,3-dihydrobenzimidazol-2-one	HCID 86729251	72.9%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 5-bromo-1H-benzo[d]imidazol-2(3H)-one (200 mg, 0.489 mmol), 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-ol (100 mg), Pd(dppf)Cl2 (36 mg, 0.049 mmol), K2CO3 (202 mg, 1.47 mmol) in H2O-dioxane (1 mL/3 mL) was stirred and heated in am microwave reactor to 100° C. for 15 min. Once cooled, the solvent was removed by concentration and the crude product purified by HPLC separation to give the title compound (74 mg, 36.5%). 1HNMR (CH3OD, 400 MHz) δ: 7.49-7.10 (m, 10H), 6.98-6.92 (m, 1H), 4.76-4.42 (m, 3H), 4.20-4.09 (m, 2H), 3.98-3.89 (m, 1H), 3.62-3.48 (m, 3H), 3.36-3.14 (m, 2H). LCMS (m/z): 416.2 [M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09388173B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-4129063689784e91ad8e8ad154f29648
Source note	uspto-grants-2016_07