Dichloromethane → HCID 57755920, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	HCID 11350801	HCID 11350801	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 57755920	HCID 57755920	—

Reaction Conditions

Temperature	185 °C

Reaction Steps

The product of Example 76 (0.100 g, 0.230 mmol, 1.00 equiv), Pd(dppf)Cl2.CH2Cl2, and 3-aminoboronic acid (107 mg, 0.690 mmol, 3.00 equiv) were dissolved in dioxane (2 mL) and 1M aq. Na2CO3 (0.690 mL, 0.690 mmol, 3.00 equiv) was added. The reaction mixture was heated to 185° C. In a SmithSynthesizer for 6 minutes. The crude reaction mixture was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (30×100 Xterra prep, 25-80% CH3CN/5 mM NH4HCO3 over 18 minutes) to afford the title compound as a white solid. MS (ES+) m/e 439 [M+H]

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07560467B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-06de7c2424274d7fae6b5c6083898881
Source note	uspto-grants-2009_07