Potassium Carbonate → HCID 66563617, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(Pyridin-4-yl)boronic acid	HCID 2734379	—
Reactant	HCID 68386507	HCID 68386507	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 66563617	HCID 66563617	28.2%

Reaction Conditions

Temperature	140 °C

Reaction Steps

To a stirred solution of 4-{6-bromo-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazol-1-yl}-N-cyclopropyl-2-methylbenzamide (30.8 mg, 0.05 mmol) in NMP (2 mL) was subsequently added 24.58 mg pyridin-4-ylboronic acid (0.2 mmol, 4 eq), 12.3 mg Pd(dppf)Cl2 (0.015 mmol, 0.3 eq) and aqueous potassium carbonate solution (1M, 150 μL) in one portion at rt. After heating for 40 min at 140° C. in a microwave oven, the mixture was filtered an subjected to preparative HPLC to yield 6.77 mg (27.95%) N-cyclopropyl-2-methyl-4-{6-(pyridin-4-yl)-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazol-1-yl}benzamide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09388140B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-2f44e53de9f948a0b3d00540e987a50e
Source note	uspto-grants-2016_07