反应详情

温度

60 °C

Sodium hydride (60% in mineral oil, 10.8 mg, 0.271 mmol) was added to a solution of 6-bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 50 mg, 0.180 mmol) in DMF (780 mL). The reaction mixture was then stirred for 15 minutes at room temperature before the addition of (bromomethyl)cyclopentane (44 mg, 0.271 mmol). The reaction mixture was then stirred overnight at room temperature and for 24 hours at 60° C. Sodium hydride (60% in mineral oil, 5 mg, 0.125 mmol) was added and the reaction was stirred for another 7 hours at 60° C. The reaction mixture was then diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude was purified via Biotage silica gel column chromatography eluting with (DCM/EtOAc 99/1 to 80/20) to afford the title product as a colourless oil (45 mg, 69%). 1H NMR (500 MHz, CDCl3) d 1.10-1.19 (m, 2H), 1.46-1.64 (m, 6H), 2.24-2.33 (m, 1H), 4.03 (s, 3H), 4.09 (d, J=7.6 Hz, 2H), 6.53 (d, J=0.9 Hz, 1H), 7.45 (t, J=0.9 Hz, 1H), 7.59 (s, 1H), 7.68 (s, 1H), 8.60 (d, J=0.9 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 3.03 min, 359 [(M+H+), 100%].

1. stirringthe reaction was stirred for another 7 hours at 60° C
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with EtOAc
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude was purified via Biotage silica gel column chromatography
8. washeluting with (DCM/EtOAc 99/1 to 80/20)