Potassium Phosphate, Tribasic → 4-Chloro-2-(2,6-dichloro-4-cyclopropylphenyl)thiazolo[5,4-c]pyridine

온도

100 °C

A mixture of 4-chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine (0.20 g, 0.45 mmol), cyclopropyl boronic acid (0.051 g, 0.59 mmol), Pd(OAc)2 (0.005 g, 0.023 mmol), P(Cy)3 (tricyclohexylphosphine) (0.013 g, 0.045 mmol) and potassium phosphate tribasic (0.336 g, 1.58 mmol) in toluene (4 mL) and water (0.2 mL) was degassed with a stream of argon and then heated at 100° C. for 18 hours. After cooling to room temperature, the crude reaction mixture was filtered through Celite® washing with EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, then dried (MgSO4) and concentrated under reduced pressure. The resultant residue was combined with the crude reaction mixture (79 mg) obtained by reacting 4-chloro-2-(2,6-dichloro-4-iodophenyl)-thiazolo[5,4-c]pyridine (0.10 g, 0.23 mmol) under the same reaction conditions and purified by column chromatography on silica gel eluting with 0-30% Et2O in petroleum ether (40-60° C.) to afford the title compound as a yellow/orange solid (148 mg, 61%). LCMS (Method D): RT=4.69 min, m/z: 355 [M+H+].

1. customwas degassed with a stream of argon
2. temperatureAfter cooling to room temperature
3. customthe crude reaction mixture
4. filtrationwas filtered through Celite®
5. washwashing with EtOAc
6. extractionThe aqueous layer was extracted with EtOAc
7. washthe combined organic layers were washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated under reduced pressure
10. customreaction mixture (79 mg)
11. customobtained
12. customunder the same reaction conditions
13. custompurified by column chromatography on silica gel eluting with 0-30% Et2O in petroleum ether (40-60° C.)

ORD 기록

ord-124a2d590035451cb4552a8abf4bc059

출처 데이터셋

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08697708B2