Water → HCID 58382317、化合物
反応式
[Br:1][C:2]1[N:3]=[C:4]([C:24]2[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=2)[N:5]2[C:10]3[CH:11]=[CH:12][N:13]([S:14]([C:17]4[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[C:9]=3[N:8]=[CH:7][C:6]=12.[OH2:31]>O1CCOCC1>[Br:1][C:2]1[N:3]=[C:4]([C:24]2[C:25]([CH:30]=[O:31])=[N:26][CH:27]=[CH:28][CH:29]=2)[N:5]2[C:10]3[CH:11]=[CH:12][N:13]([S:14]([C:17]4[CH:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=4)(=[O:16])=[O:15])[C:9]=3[N:8]=[CH:7][C:6]=12参加物
4
反応条件
- 温度
- 105 °C
実験手順
The 3-bromo-1-(2-methylpyridin-3-yl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.500 g, 1.03 mmol, prepared using J.1 from Example #2, Step B with 2-methylnicotinic acid, L.2 with POCl3 and AB) in 1,4-dioxane (20 mL) was treated with SeO2 (0.210 g, 1.89 mmol) then the mixture was heated at about 105° C. for about 1 h. The mixture was cooled to rt then water (0.6 mL) was added. The mixture was heated to reflux for about 3 days. The mixture was cooled to rt then concentrated in vacuo. The material was purified using a 10 g silica column eluting with EtOAc. The impure fractions were combined and concentrated then the material was purified using a 10 g silica column eluting with EtOAc. The materials were combined to give 3-(3-bromo-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)picolinaldehyde (0.355 g, 69%): LC/MS (Table 2, Method b) Rt=3.53 min; MS m/z 480 (M+H)+.