Dichloromethane → Ethyl 4-methyl-5-(spiro[4.5]dec-7-en-8-yl)isoxazole-3-carboxylate

To a 2-5 mL microwave vial containing a solution of 4,4,5,5-tetramethyl-2-(spiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (168 mg, 0.641 mmol) in MeCN (2 mL), ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (150 mg, 0.641 mmol) was added followed by K2CO3 (266 mg, 1.923 mmol), PdCl2(dppf).CH2Cl2 adduct (Alfa Aesar) (52.3 mg, 0.064 mmol) and water (1 mL). The vial was flushed with nitrogen, sealed and treated in the microwave (Biotage Smith Initiator) at 90° C. for 1 hour. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL) and the organic phase was washed with brine (20 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give an orange oil. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-30% EtOAc in iso-hexane afforded the title compound;

1. additionwas added
2. customThe vial was flushed with nitrogen
3. customsealed
4. additiontreated in the microwave (Biotage Smith Initiator) at 90° C. for 1 hour
5. customThe reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL)
6. washthe organic phase was washed with brine (20 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto give an orange oil
11. customThe crude material was adsorbed onto silica and purification by chromatography
12. washeluting with 0-30% EtOAc in iso-hexane

ORD-Eintrag

ord-46be4304ecb1432689237f5edfee5083

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09403810B2