Potassium Phosphate, Tribasic → US10023592, Example 237

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	7-Bromo-5-methyl-[1,3]oxazolo[4,5-c]pyridin-4-one	HCID 84726089	—
Reactant	2-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 123434859	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	US10023592, Example 237	HCID 118022201	20%

Reaction Conditions

Temperature	60 °C

Reaction Steps

The title compound of step 5 (60 mg, 0.3 mmol) in dioxane (2 mL) and H2O (0.4 mL) was stirred at 15° C. under N2 for 30 min. Pd(dppf)Cl2 (19 mg, 0.026 mmol), the title compound of Example 90, step 1 (120 mg, 0.3 mmol) and K3PO4 (166 mg, 0.8 mmol,) were added at 15° C. under N2. The reaction mixture was heated at 60° C. for 12 h. Purification by silica gel chromatography (EA) and preparative HPLC gave the title compound (20.63 mg, 20%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.03 (d, J=2.0 Hz, 1H), 8.02 (s, 1H), 7.96 (dd, J1=8.4 Hz, J2=2.0 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 3.96 (d, J=6.8 Hz, 2H), 3.76 (s, 3H), 3.1 (s, 3H), 1.18 (m, 1H), 0.60 (m, 2H), 0.30 (m, 2H). LCMS: 375.1 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115114B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-d268b73114df41d1ba8a802e43ebd5cc
Source note	uspto-grants-2015_08