Dimethyl Sulfoxide → (S)-7-bromo-3-(neopentyloxy)-2',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,3'-[1,4]oxazin]-5'-amine

A vial was charged with 2,2-dimethylpropan-1-ol (100 mg, 1.130 mmol) and DMSO (1130 μL). Sodium hydride (60% in mineral oil; 45.2 mg, 1.130 mmol) was added. The vial was placed in a 100° C. oil bath for 5 min. the reaction mixture was cooled to room temperature and (S)-7-bromo-3-chloro-2′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazin]-5′-amine (86 mg, 0.226 mmol) was added in one portion. The vial was sealed and heated in a 100° C. oil bath for 2 h. The mixture was cooled to room temperature, then diluted with water and EtOAc. Brine was added, and the layers were separated. The aq. layer was extracted with EtOAc (2×). The combined organic extracts were dried over sodium sulfate, and concentrated. The residue was purified by chromatography (0-100% EtOAc/Hexane) to give (S)-7-bromo-3-(neopentyloxy)-2′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazin]-5′-amine as a light-yellow solid.

1. customwas placed in a 100° C.
2. customfor 5 min.
3. customThe vial was sealed
4. temperatureheated in a 100° C. oil bath for 2 h
5. temperatureThe mixture was cooled to room temperature
6. customthe layers were separated
7. extractionThe aq. layer was extracted with EtOAc (2×)
8. dry with materialThe combined organic extracts were dried over sodium sulfate
9. concentrationconcentrated
10. customThe residue was purified by chromatography (0-100% EtOAc/Hexane)

ORD-Eintrag

ord-2db3a50e520e4bdf8917f1a5aa4612bb

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08497264B2