Sodium Azide → Methyl 7-fluoro-6-(2-fluorophenylamino)-3-methylbenzo[c]isoxazole-5-carboxylate

To a solution of methyl 5-acetyl-3,4-difluoro-2-(2-fluorophenylamino)benzoate (example 3, step D) (1.50 g, 4.64 mmol) in a mixture of acetone (36 ml) and H2O (12 ml) was added NaN3 (452 mg, 6.96 mmol). The reaction was heated at 65° C. for 16 h and cooled to room temperature. Acetone was concentrated and the resulting mixture was extracted with EtOAc (2×50 ml). The combined organic solution was washed with brine (50 ml), dried over MgSO4 and concentrated to give a yellow solid. To the solid was added H2O (24 ml) and the reaction was heated at reflux for 3 h. The reaction was cooled to room temperature, filtered, and washed with H2O. The resulting solid was dried under high vacuum with P2O5 at 65° C. for 24 h to give 1.31 g (89%) of methyl 7-fluoro-6-(2-fluorophenylamino)-3-methylbenzo[c]isoxazole-5-carboxylate as a yellow solid.

1. temperaturecooled to room temperature
2. concentrationAcetone was concentrated
3. extractionthe resulting mixture was extracted with EtOAc (2×50 ml)
4. washThe combined organic solution was washed with brine (50 ml)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customto give a yellow solid
8. temperaturethe reaction was heated
9. temperatureat reflux for 3 h
10. temperatureThe reaction was cooled to room temperature
11. filtrationfiltered
12. washwashed with H2O
13. dry with materialThe resulting solid was dried under high vacuum with P2O5 at 65° C. for 24 h

ORDレコード

ord-ce8182ffd33a4e379af292dcbda6218e

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08063049B2