Cesium carbonate → Tert-butyl 4-[5-(3-amino-5-methylphenyl)-1,3-thiazol-2-yl]-4-hydroxycyclohexanecarboxylate

온도

100 °C

To a flask containing 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.6 g, 6.96 mmol), the product of Step 2 (2.52 g, 6.96 mmol), dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane (0.33 g, 0.70 mmol), Pd2(dba)3 (0.32 g, 0.35 mmol), cesium carbonate (6.80 g, 20.9 mmol) was added a degassed mixture of dioxane (23 mL) and water (2.3 mL). The solution was evacuated and then purged with argon 5 times and then heated at 100° C. overnight. The reaction was then cooled to room temperature, diluted with ethyl aceate, washed with aqueous saturated sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield tert-butyl 4-[5-(3-amino-5-methylphenyl)-1,3-thiazol-2-yl]-4-hydroxycyclohexanecarboxylate. MS ESI: [M+H]+ m/z 389.

1. customThe solution was evacuated
2. custompurged with argon 5 times
3. temperatureThe reaction was then cooled to room temperature
4. additiondiluted with ethyl aceate
5. washwashed with aqueous saturated sodium bicarbonate
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customFlash chromatography was used for purification

ORD 기록

ord-70b671e377ba4f7796edb6859dbd0b68

출처 데이터셋

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08551984B2