Acetic Acid → (4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine

온도

40 °C

4-Bromo-6-chloro-quinolin-2-ylamine (3.12 g, 12 mmol) was dissolved in 100 mL 1,2-dichloroethane. 2-Methoxybenzaldehyde (1.98 g, 15 mmol) and acetic acid (2.91 g, 48 mmol) were added. The reaction mixture was stirred at 40° C. for 3 h. Sodium triacetoxy borohydride (5.99 g, 25 mmol) was added and stirring was continued at room temperature overnight. The reaction mixture was quenched by addition of 200 mL sat. sodiumbicarbonate solution. The mixture was extracted three times with dichloromethane (200 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). (4-Bromo-6-chloro-quinolin-2-yl)-(2-methoxy-benzyl)-amine was obtained as an off-white solid (2.2 g, 48%), MS: m/e=379.1 (M+H+).

1. stirringstirring
2. waitwas continued at room temperature overnight
3. customThe reaction mixture was quenched by addition of 200 mL sat. sodiumbicarbonate solution
4. extractionThe mixture was extracted three times with dichloromethane (200 mL each)
5. dry with materialdried with sodium sulfate
6. filtrationfiltered
7. customevaporated
8. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

ORD 기록

ord-47ca78fdd5c34dd3a0858b5eb7b6c360

출처 데이터셋

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08399674B2