Water → 6,6-dimethyl-2-(6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 2795311	—
Reactant	2-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-one	HCID 68597236	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	6,6-dimethyl-2-(6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one	HCID 44580721	34%

Reaction Steps

A stirred solution of Example 39 (0.055 g, 0.14 mmol), 1,3,5-trimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.066 g, 0.28 mmol), potassium phosphate (0.089 g, 0.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.05 g, 0.004 mmol) in DME (4 mL) and water (1 mL) was heated to 140° C. under microwave irradiation in a sealed tube for 30 minutes, and then concentrated in vacuo. Purification by preparative HPLC (Method 7) gave the title compound (0.020 g, 34%) as an off-white solid. δH (CDCl3) 7.84 (1H, d, J 1.9 Hz), 7.08-6.99 (2H, m), 5.45 (1H, s), 4.43-4.35 (2H, m), 4.22-4.16 (2H, m), 3.79 (3H, s), 2.87 (2H, s), 2.29 (6H, s), 1.40 (6H, s). LCMS (ES+) 424.0 (M+H)+, RT 3.17 minutes (Method 2).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08242116B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-c1150b297da94ad091ae8d03558dcda0
Source note	uspto-grants-2012_08