Sodium periodate → 3-Isopropyl-[1,2,4]triazolo[4,3-b]pyridazine-6-carbaldehyde

HRID 1929961노트

반응식

HRID 1929961 반응식
[CH:1]([C:4]1[N:8]2[N:9]=[C:10]([CH:13]=C)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:16].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH:1]([C:4]1[N:8]2[N:9]=[C:10]([CH:13]=[O:16])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 23667635Sodium periodateHCID 579298913-Isopropyl-6-vinyl-[1,2,4]triazolo[4,3-b]pyridazine

생성물 1

HCID 579298993-Isopropyl-[1,2,4]triazolo[4,3-b]pyridazine-6-carbaldehyde수율 69.5%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

The 3-isopropyl-6-vinyl-[1,2,4]triazolo[4,3-b]pyridazine (3.28 g, 17.4 mmol, Preparation #1) in 1,4-dioxane (75 mL) and water (15 mL) was treated with osmium tetroxide (3.5 mL, 0.28 mmol, 2.5 wt % in 2-methyl 1-propanol) and then sodium periodate (7.45 g, 34.9 mmol) was added. The mixture was stirred at ambient temperature for about 1 h and then diluted with 1,4-dioxane (50 mL) and filtered through Celite®. The filter cake was washed with 1,4-dioxane then EtOAc. The filtrate was concentrated under reduced pressure and then the residue was purified by flash chromatography on silica gel with DCM/MeOH (9:1) as an eluent to give the title compound (2.30 g, 69.4%) as a beige solid: 1H NMR (CDCl3) δ 1.61 (d, 6H), 3.76 (m, 1H), 7.65 (d, 1H), 8.21 (m, 1H), 10.06 (d, 1H).

후처리

  1. filtrationfiltered through Celite®
  2. washThe filter cake was washed with 1,4-dioxane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel with DCM/MeOH (9:1) as an eluent

출처 및 근거

ORD 기록
ord-dc966c3ffdd04a069d734e43f2865962
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188083B2

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