Diisopropylethylamine → 2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 2734620	—
Reactant	2-methyl-5-(trifluoromethyl)-1,3-oxazole-4-carboxylic Acid	HCID 2775651	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Sodium chloride; water	HCID 57417360	—
Product	2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(trifluoromethyl)oxazole-4-carboxamide	HCID 86700837	47%

Reaction Steps

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (420 mg, 1.917 mmol) in anhydrous DMF (9.6 mL) was added 2-methyl-5-(trifluoromethyl)oxazole-4-carboxylic acid (449 mg, 2.300 mmol) followed by DIPEA (1.0 mL, 5.75 mmol) and the mixture was stirred at room temperature for 10 minutes. HATU (875 mg, 2.300 mmol) was added and the mixture stirred at room temperature for 16 hours. The mixture was taken up in 1:1 mixture of brine and water and extracted with EtOAc. The organic portion was dried over sodium sulfate, filtered and concentrated to afford a brown oil, which was purified by flash column chromatography to afford the title compound as pale yellow solid after drying (360 mg, 47% yield). LC/MS, ESI-MS(+): 397.1, RT: 1.49 (Condition E).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08993619B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-acddda486ab8432eba5665004956429a
Source note	uspto-grants-2015_03