Diisopropylethylamine → (R)-tert-butyl 1-(3-bromo-4-cyanophenylamino)-3-methoxypropan-2-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Bromo-4-fluorobenzonitrile	HCID 118939	—
Reactant	tert-butyl N-((2R)-1-amino-3-methoxypropan-2-yl)carbamate	HCID 59199768	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(R)-tert-butyl 1-(3-bromo-4-cyanophenylamino)-3-methoxypropan-2-ylcarbamate	HCID 67775752	78.1%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 2-bromo-4-fluorobenzonitrile (0.2 g, 1 mmol) in DMSO (3 mL) was added (R)-tert-butyl 1-amino-3-methoxypropan-2-ylcarbamate (0.22 g, 1.08 mmol) and DIPEA (0.267 mL, 1.5 mmol). The mixture was heated at 100° C. for 15 h, and was diluted with EtOAc and washed with 1N HCl and Sat. NaHCO3. The organic phase was separated, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 1-(3-bromo-4-cyanophenylamino)-3-methoxypropan-2-ylcarbamate (0.3 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846928B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-5a25b2abd4604e2d9bad68ab2fc3a528
Source note	uspto-grants-2014_09