Dimethylformamide → HCID 67325513, compound

Thionyl chloride (0.679 mL, 9.30 mmol) was added to a solution of 2-bromo-3-methylbenzoic acid (2.0 g, 9.30 mmol) and DMF (0.072 mL, 0.930 mmol) in DCM (100 mL) at 0° C. The reaction mixture was allowed to warm to RT and stirred for 1 h and then cooled to 0° C. before DIPEA (3.25 mL, 18.60 mmol) followed by 2-propynylamine (0.766 mL, 11.16 mmol) were added. The resulting solution was stirred for 45 min at 0° C. The reaction mixture was diluted with saturated ammonium chloride and water and then extracted with EtOAc. The combined organic extracts were washed with saturated ammonium chloride, water, saturated sodium bicarbonate, saturated sodium chloride and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material as a tan solid. The crude product was dissolved in dioxane (100 mL) and cooled to 0° C. Sodium hydride (0.409 g, 10.23 mmol) was added and the mixture was stirred at RT for 30 min before bringing to a reflux. After 5 h, the reaction is concentrated. The crude material was purified by silica gel chromatography to provide 2-(2-bromo-3-methylphenyl)-5-methyloxazole.

1. additionwere added
2. stirringThe resulting solution was stirred for 45 min at 0° C
3. extractionextracted with EtOAc
4. washThe combined organic extracts were washed with saturated ammonium chloride, water, saturated sodium bicarbonate, saturated sodium chloride
5. dry with materialdried over sodium sulfate
6. filtrationThe solution was filtered
7. concentrationconcentrated in vacuo
8. customto give the crude material as a tan solid
9. temperaturecooled to 0° C
10. stirringthe mixture was stirred at RT for 30 min
11. waitAfter 5 h
12. concentrationthe reaction is concentrated
13. customThe crude material was purified by silica gel chromatography

ORD record

ord-7d44f088e1c741d5ab4739ff50a8357f

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735384B2