Tris(1,1-dimethylethyl)phosphine → HCID 135524916, compound

Participants

Role	Name	HCID	Charge
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(Pyrimidin-5-yl)boronic acid	HCID 2795193	—
Reactant	HCID 136066551	HCID 136066551	—
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	HCID 135524916	HCID 135524916	10%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a solution of 5-bromo-3-[4-(2,3-difluoro-phenyl)-isoxazol-5-yl]-1H-pyrrolo[2,3-b]pyridine (prepared by Method A, 50 mg, 0.13 mmol) and 5-pyrimidine boronic acid (33 mg, 0.27 mmol) in DME (1 mL) was added sat. NaHCO3 (1.2 M, 0.54 mL, 0.65 mmol) and tri-tert-butylphosphine (27 mg, 0.13 mmol). The suspension was stirred under N2 atmosphere while catalyst PdCl2(dppf) (5 mg, 0.006 mmol) was added. The reaction mixture was then heated at 80° C. for 5 h and diluted with ethyl acetate. The inorganic salt was removed by filtration, the filtrate was evaporated and purified by HPLC to afford the desired product as off-white solid (5.0 mg, 0.013 mmol, 10%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07446199B2
Source dataset	uspto-grants-2008_11
ORD ID	ord-853e906c1af94bfbb0e8f1fe82b426fa
Source note	uspto-grants-2008_11