Dichloromethane → HCID 53379558, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	N-Ethyl-N'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea	HCID 44119377	—
Reactant	3-(2-Chloropyrimidin-4-yl)-8-oxa-3-azabicyclo[3,2,1]octane	HCID 66371527	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	HCID 53379558	HCID 53379558	—

Reaction Steps

3-(2-chloropyrimidin-4-yl)-8-oxa-3-azabicyclo[3,2,1]octane (intermediate 24) (100 mg, 0.44 mmol) was stirred with 1-ethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (141 mg, 0.48 mmol), Pd(dppf)Cl2:DCM (18 mg, 0.002) and Na2CO3(140 mg, 1.3 mmol) in DME:Water (4:1) for 30 minutes at 130° C. in microwave conditions. The reaction mixture was filtered through a celite545 cake and washed with methanol. The reaction mixture was concentrated in vacuo. The resulting oil was purified by prep HPLC at low pH to afford the title compound as a white solid. (20 mg, 13%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249129B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-768c6b4f279948de851cf04a36db32d5
Source note	uspto-grants-2016_02