Water → 5-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazole

HRID 246614

반응식

HRID 246614 반응식
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[I:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O([C:21](C)(C)C)[K].CI.O>C1COCC1>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:21])[N:13]=[C:12]2[I:18])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 178418922HCID 178418922, 화합물HCID 178455023HCID 178455023, 화합물

생성물 1

HCID 712798665-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazole수율 80.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-(tert-butyldimethylsilyloxy)-3-iodo-1H-indazole (3 g, 8.0 mmol) in THF (25 mL) was added KO-tBu (1.28 g, 11.2 mmol) at 0° C. followed by addition of MeI (1.58 g, 11.2 mmol), after the addition, the reaction mixture was warmed to room temperature and stirred for 4 hours, then H2O (25 mL) was added to the mixture and product extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure, the residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with petroleum ether/EtOAc=5:1) to give 5-(tert-butyldimethylsilyloxy)-3-iodo-1-methyl-1H-indazole (2.5 g, 80.3%) as a white solid. (M+H)+=389; 1H NMR (300 MHz, CDCl3), δ 7.22-7.19 (m, 1H), 7.03-7.01 (m, 1H), 6.80 (s, 1H), 4.05 (s, 3H), 1.01 (s, 9H), 0.23 (s, 6H).

후처리

  1. additionafter the addition
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with petroleum ether/EtOAc=5:1)

출처 및 근거

ORD 기록
ord-a51d39fae6224988a1ab16c25e5e8671
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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