Potassium Carbonate → HCID 69675359, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	tert-Butyl (2S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate	HCID 56605192	—
Reactant	HCID 67681755	HCID 67681755	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 69675359	HCID 69675359	33.8%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5,9,10-tetrahydropyren-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (139 mg, 0.22 mmol) and (S)-tert-butyl 2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (77 mg, 0.24 mmol) were dissolved in dioxane (2 mL) and DMSO (2 mL). Pd(dppf)2Cl2 (16 mg, 0.022 mmol), Pd(PPh3)4 (25 mg, 0.022 mmol), and K2CO3 (2M in H2O, 0.33 mL, 0.66 mmol). The tube was sealed and heated to 100° C. for 20 h. The mixture was cooled to rt, diluted with EtOAc, and washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography to yield product (54.5 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09156823B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-684d96f09f63465dbf827cea9ea93dac
Source note	uspto-grants-2015_10