Benzophenone imine → 1-Methyl-1H-indazol-3-amine

A mixture of palladium(II) acetate (82 mg, 2 mol %) and Xantphos (287 mg, 3 mol %) in toluene (10 mL) was stirred for 5 min at ambient temperature. To the solution was added a solution of Example 1F (3.68 g, 17.4 mmol) and benzophenone imine (3.00 g, 17.4 mmol) in toluene (30 mL). The mixture was evacuated and purged with nitrogen two times, then stirred at ambient temperature for 15 min Sodium tert-butoxide (1.90 g, 24.4 mmol) was added and the mixture was evacuated and purged with nitrogen. The mixture was heated to between 80 and 85° C. for 2 h, cooled to ambient temperature, and diluted with water (30 mL). The layers were partitioned and the aqueous layer was extracted with additional toluene (20 mL). The combined organic layers were stirred with 6 N HCl (10 mL) for 1 h, then 40 mL of water was added to dissolve the solids. The toluene layer was discarded and aqueous layer filtered to remove insoluble material. The aqueous layer was adjusted to pH 14 with the addition of 50% NaOH and the resulting solid was filtered and dried to provide the title compound. MS (DCI/NH3) m/z 202 (M+H)+.

1. customThe mixture was evacuated
2. custompurged with nitrogen two times
3. additionwas added
4. customthe mixture was evacuated
5. custompurged with nitrogen
6. temperatureThe mixture was heated to between 80 and 85° C. for 2 h
7. temperaturecooled to ambient temperature
8. additiondiluted with water (30 mL)
9. customThe layers were partitioned
10. extractionthe aqueous layer was extracted with additional toluene (20 mL)
11. stirringThe combined organic layers were stirred with 6 N HCl (10 mL) for 1 h
12. addition40 mL of water was added
13. dissolutionto dissolve the solids
14. filtrationaqueous layer filtered
15. customto remove insoluble material
16. additionThe aqueous layer was adjusted to pH 14 with the addition of 50% NaOH
17. filtrationthe resulting solid was filtered
18. customdried

ORD 기록

ord-acb7ab7dac3345708c862d049f4f323f

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08604053B2