Cesium carbonate → 5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)-phenyl)picolinonitrile

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Cyanopyridine-5-boronic acid pinacol ester	HCID 16414188	—
Reactant	(2S,1R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol	HCID 45257860	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl)-phenyl)picolinonitrile	HCID 71050047	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of commercially available 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (0.5 g, 2.17 mmol) in degassed dimethoxyethane (10 mL) and water (3 mL) is added (1R,2S)-2-amino-3-fluoro-1-(4-iodophenyl)-propan-1-ol (0.65 g, 2.20 mmol) and Cs2CO3 (2.15 g, 6.6 mmol). Pd(PPh3)4 (0.25 g, 0.21 mmol) is added and the reaction mixture heated to 90° C. for 1.5 hours.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09340564B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-128efe3028614e3b9aba106749f5e592
Source note	uspto-grants-2016_05