Sodium Carbonate → 5-(2-(4-Aminophenoxy)pyridin-3-yl)thiazol-2-amine

온도

100 °C

In a 20 mL sealed tube was added dioxane (1.0 mL), purged solvent with nitrogen for 5 minutes and the tube was sealed. 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzenamine (0.144 g, 0.462 mmol), 5-bromothiazol-2-amine hydrobromide (0.100 g, 0.385 mmol), 2.0M aqueous sodium carbonate (0.385 mL) was added and the tube was purged flask with nitrogen, and again sealed. Tris(dibenzylideneacetone)dipalladium (0) (0.026 g, 0.029 mmol), tri-t-butylphosphonium tetrafluoroborate (0.025 g, 0.087 mmol) was added and the tube was purged with nitrogen, sealed and heated to 100° C. while stirring for 5 hours. The mixture was cooled to RT, passed through pad of silica, washing with 90:10:1 (CH2Cl2: MeOH: NH4OH). The eluent was concentrated and the product was purified by silica gel chromatography eluting with 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2. The product fractions were concentrated to yield 5-(2-(4-aminophenoxy)pyridin-3-yl)thiazol-2-amine as tan solid. MS m/z=285[M+1]+. Calc'd for C14H12N4OS: 284.34.

1. customIn a 20 mL sealed tube
2. custompurged solvent with nitrogen for 5 minutes
3. customthe tube was sealed
4. customthe tube was purged flask with nitrogen
5. customagain sealed
6. customthe tube was purged with nitrogen
7. customsealed
8. temperatureThe mixture was cooled to RT
9. washwashing with 90:10:1 (CH2Cl2: MeOH: NH4OH)
10. concentrationThe eluent was concentrated
11. customthe product was purified by silica gel chromatography
12. washeluting with 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2
13. concentrationThe product fractions were concentrated

ORD 기록

ord-8d9359a960f2495e8507b710acf2f2c0

출처 데이터셋

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08022221B2