Dichloromethane → US9156811, Ddd86206

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2-(1-Piperaziny) pyridine-4-boronic acid pinacol ester	HCID 16217948	—
Reactant	3'-Formyl-biphenyl-4-sulfonic acid methyl-(1,3,5-trimethyl-1h-pyrazol-4-yl)-amide	HCID 90717095	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	US9156811, Ddd86206	HCID 46179031	1,483.3%

Reaction Steps

Prepared from the sulphonamide of intermediate 3 (500 mg, 1.3 mmol), 2-(1-piperazinyl)pyridine-4-boronic acid pinacol ester (580 mg, 2.0 mmol), tribasic potassium phosphate (427 mg, 2.0 mmol), and Pd(dppf)Cl2.DCM (50 mg, 0.06 mmol) in DMF (3.0 ml) and water (0.75 ml), according to the method of intermediate 11, to give the title compound as an off-white powder (412 mg, 0.89 mmol, 68%). δH (D-6 DMSO, 300K) 8.20 (1H, d J 5.2 Hz), 8.14 (1H, d J 1.7 Hz), 7.84 (1H, dd J 1.75 Hz 8.3 Hz), 7.79 (1H, d J 8.3 Hz), 7.13 (1H, s), 6.99 (1H, dd J 1.15 Hz 5.2 Hz), 3.55 (3H, s), 3.51 (4H, s br), 2.79 (4H, s br), 1.90 (3H, s), 1.69 (3H, s). m/z (ES+, 70V) 461.2 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09156811B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-ec606811be354cb7b0843fad1267b6c3
Source note	uspto-grants-2015_10