Sodium Carbonate → Methyl2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

To a microwave vial containing methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (100 mg, 0.26 mmol), 6-bromopyridin-3-amine (49 mg, 0.28 mmol) and Pd2(PPh3)4 (60 mg, 0.05 mmol) was added 1,4-dioxane (1.3 ml) at room temperature. 2N sodium carbonate (0.39 ml, 0.78 mmol) was added and the mixture was subjected to microwave radiation at 120° C. for 50 minutes. The resulting mixture was concentrated to dryness and taken up in EtOAc, the slurry was dried over sodium sulfate and filtered through a pad of celite. The filtrate was concentrated and purified by column chromatography to afford the title compound (120 mg, 65% yield). LC/MS, ESI-MS(+): 353.4, RT: 1.12 (Condition E).

1. customat 120° C.
2. customfor 50 minutes
3. concentrationThe resulting mixture was concentrated to dryness
4. dry with materialthe slurry was dried over sodium sulfate
5. filtrationfiltered through a pad of celite
6. concentrationThe filtrate was concentrated
7. custompurified by column chromatography

ORD 기록

ord-c383c490c51440139d42ba3711ecb3d4

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08993619B2