Bromobenzene → 1-[6-Chloro-1-(2-methoxy-ethoxymethyl)-5-phenylamino-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

온도

50 °C

An oven-dried flask was charged with 1-[5-amino-6-chloro-1-(2-methoxy-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (Intermediate from Example 41, product from Step A) (0.100 g, 0.254 mmol), bromobenzene (43.8 mg, 0.279 mmol), Pd(dba)2 (1.50 mg, 2.50 μmol), Q-Phos (3.60 mg, 5.10 μmol), and sodium tert-butoxide (36.6 mg, 0.381 mmol). The flask was purged with N2. Dry toluene (0.5 mL) was added and the slurry was briefly sonicated. The reaction mixture was heated at 50° C. for 18 h. The reaction mixture was then diluted with dichloromethane and filtered through a pad of Celite®. The filter cake was rinsed with EtOAc and the filtrate was concentrated under reduced pressure. The residue was purified (FCC) (10-45% EtOAc/hexanes) to yield the titled compound (7.1 mg, 6% yield), which was used in the next step without further purification. MS (ESI/CI): mass calcd. for C23H24ClN5O4, 469.2; m/z found, 470.1 [M+H]+.

1. customThe flask was purged with N2
2. additionDry toluene (0.5 mL) was added
3. customthe slurry was briefly sonicated
4. additionThe reaction mixture was then diluted with dichloromethane
5. filtrationfiltered through a pad of Celite®
6. washThe filter cake was rinsed with EtOAc
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue was purified (FCC) (10-45% EtOAc/hexanes)

ORD 기록

ord-606669dcb6f4465988bbf887c2e190d0

출처 데이터셋

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09073923B2