2-Iodoxybenzoic acid → (6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanone

HRID 69242

반응식

HRID 69242 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:21]=[CH:20][C:19]4[C:15](=[CH:16][N:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]=4)[CH:14]=3)[OH:12])=[CH:9][N:10]=2)[N:7]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:21]=[CH:20][C:19]4[C:15](=[CH:16][N:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]=4)[CH:14]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1

참가 물질

4

반응물 2

HCID 1087942-Iodoxybenzoic acidHCID 87523362(Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanol

생성물 1

HCID 87523378(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanone

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-methanol (Stage 195.4, 580 mg, 1.349 mmol) was dissolved in acetone (40 mL) and heated 1 h to reflux together with 2-iodoxybenzoic acid (1.133 g, 4.05 mmol). The RM was cooled down to rt and the acetone was removed under reduced pressure. The residue was mixed with 2 M NaOH solution and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=50:50->0: 100) to afford the title compound as a light brown foam (tR 7.11 min (conditions 3), MH+=428).

후처리

  1. temperatureheated 1 h
  2. customthe acetone was removed under reduced pressure
  3. additionThe residue was mixed with 2 M NaOH solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=50:50->0: 100)

출처 및 근거

ORD 기록
ord-31302cce90154816ad01c97c5ad7d61b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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