Trimethylsilyl iodide → 3-{4-[(Dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20542노트

반응식

HRID 20542 반응식
[CH3:1][N:2]([CH3:34])[S:3]([C:6]1[CH:33]=[CH:32][C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][O:29]C)[CH:25]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[O:15])=[CH:8][CH:7]=1)(=[O:5])=[O:4].I[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:34][N:2]([CH3:1])[S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:31])[CH2:28][OH:29])[CH:25]=2)[C:14]([NH:16][C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[O:15])=[CH:32][CH:33]=1)(=[O:4])=[O:5]

참가 물질

5

반응물 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 115983163-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

생성물 1

HCID 115473993-{4-[(Dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide수율 45.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 3-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (500 mg, 1.0 mmol) in acetonitrile (30 mL) was added iodotrimethylsilane (0.73 mL, 1.0 g, 5.1 mmol) dropwise. The resulting mixture was stirred at RT for 20 hours. Aqueous sodium hydrogen carbonate solution (saturated, 5 mL) was added slowly and the resulting mixture was concentrated under reduced pressure. Water (50 mL) was added and the mixture was extracted with ethyl acetate (50 mL). The organic layers was washed with brine (50 mL), dried (MgSO4) and evaporated to afford the crude product. This was purified by flash chromatography (eluting with an increasing gradient of 60 to 100% ethyl acetate in isohexane) to afford the pure title compound (216 mg, 45%).

후처리

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. additionWater (50 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (50 mL)
  4. washThe organic layers was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto afford the crude product
  8. customThis was purified by flash chromatography (
  9. washeluting with an increasing gradient of 60 to 100% ethyl acetate in isohexane)

출처 및 근거

ORD 기록
ord-60a155fcb74746c3abc4c5795b20f29d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

반응 노트

불러오는 중…