Potassium Phosphate, Tribasic → (S)-7-(3,4-difluorophenyl)-3-methoxy-2',6'-dihydrospiro[chromeno[2,3-c]pyridine-5,3'-[1,4]oxazin]-5'-amine

温度

100 °C

A microwave vial was charged with (S)-7-bromo-3-methoxy-2′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazin]-5′-amine (0.075 g, 0.199 mmol). 3,4-difluorophenylboronic acid (0.063 g, 0.399 mmol), potassium phosphate (0.127 g, 0.598 mmol), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (7.06 mg, 9.97 μmol) were added. The vial was flushed with Ar (g), then dioxane (0.748 mL) and water (0.249 mL) were added in sequence. The vial was sealed and heated in a Biotage Initiator microwave reactor for 30 min at 100° C. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (0-100% EtOAc/Hexanes) to afford (S)-7-(3,4-difluorophenyl)-3-methoxy-2′,6′-dihydrospiro[chromeno[2,3-c]pyridine-5,3′-[1,4]oxazin]-5′-amine (0.073 g, 0.178 mmol, 89% yield) as an off-white solid. [M+H]+=410.4

1. customThe vial was flushed with Ar (g)
2. additiondioxane (0.748 mL) and water (0.249 mL) were added in sequence
3. customThe vial was sealed
4. additionThe reaction was diluted with ethyl acetate
5. washwashed with water
6. extractionThe aqueous layer was extracted with ethyl acetate
7. washthe combined organic layers were washed with brine
8. dry with materialdried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe material was purified via column chromatography (0-100% EtOAc/Hexanes)

ORDレコード

ord-d6bf8de29c084e019b22fea9f50dc27b

出典データセット

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09012446B2